{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T02:14:47Z","timestamp":1790820887384,"version":"4.1.0"},"reference-count":160,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2020,11,1]],"date-time":"2020-11-01T00:00:00Z","timestamp":1604188800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100004484","name":"Tehran University of Medical Sciences and Health Services","doi-asserted-by":"publisher","award":["98-02-33-42922"],"award-info":[{"award-number":["98-02-33-42922"]}],"id":[{"id":"10.13039\/501100004484","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2020,11]]},"DOI":"10.1016\/j.bioorg.2020.104240","type":"journal-article","created":{"date-parts":[[2020,8,27]],"date-time":"2020-08-27T21:47:12Z","timestamp":1598564832000},"page":"104240","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":282,"special_numbering":"C","title":["History of the development of antifungal azoles: A review on structures, SAR, and mechanism of action"],"prefix":"10.1016","volume":"104","author":[{"given":"Mohammad","family":"Shafiei","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lee","family":"Peyton","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mehrnoosh","family":"Hashemzadeh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alireza","family":"Foroumadi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bioorg.2020.104240_b0005","first-page":"4","volume":"13","author":"Brown","year":"2012","journal-title":"Supplementary Materials for Hidden Killers : Human Fungal Infections"},{"key":"10.1016\/j.bioorg.2020.104240_b0010","doi-asserted-by":"crossref","first-page":"5678","DOI":"10.1016\/j.bmc.2012.04.045","article-title":"The biology and chemistry of antifungal agents: A review","volume":"20","author":"Kathiravan","year":"2012","journal-title":"Bioorganic Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0015","doi-asserted-by":"crossref","unstructured":"N. Thamban Chandrika, E.K. Dennis, S.K. Shrestha, H.X. Ngo, K.D. Green, S. Kwiatkowski, A.G. Deaciuc, L.P. Dwoskin, D.S. Watt, S. Garneau-Tsodikova, N,N\u2032-diaryl-bishydrazones in a biphenyl platform: Broad spectrum antifungal agents, Eur. J. Med. Chem. (2019) 273\u2013281. doi:10.1016\/j.ejmech.2018.12.042.","DOI":"10.1016\/j.ejmech.2018.12.042"},{"key":"10.1016\/j.bioorg.2020.104240_b0020","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1038\/nrd.2017.46","article-title":"The antifungal pipeline: A reality check","volume":"16","author":"Perfect","year":"2017","journal-title":"Nat. Rev. Drug Discov."},{"key":"10.1016\/j.bioorg.2020.104240_b0025","doi-asserted-by":"crossref","first-page":"48","DOI":"10.3390\/microorganisms5030048","article-title":"Phosphate Acquisition and Virulence in Human Fungal Pathogens","volume":"5","author":"Ikeh","year":"2017","journal-title":"Microorganisms."},{"key":"10.1016\/j.bioorg.2020.104240_b0030","doi-asserted-by":"crossref","unstructured":"G.D. Brown, D.W. Denning, S.M. Levitz, Tackling human fungal infections, Science (80-.). 336 (2012) 647. doi:10.1126\/science.1222236.","DOI":"10.1126\/science.1222236"},{"key":"10.1016\/j.bioorg.2020.104240_b0035","first-page":"1","article-title":"Unmet Clinical Needs, and New Approaches","author":"Roemer","year":"2014","journal-title":"Cold Spring Harb Perspect Med."},{"key":"10.1016\/j.bioorg.2020.104240_b0040","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1080\/13693780701218689","article-title":"Nosocomial fungal infections: Epidemiology, diagnosis, and treatment","volume":"45","author":"Perlroth","year":"2007","journal-title":"Med. Mycol."},{"key":"10.1016\/j.bioorg.2020.104240_b0045","doi-asserted-by":"crossref","first-page":"791","DOI":"10.2217\/fmb.14.32","article-title":"Antifungal drug discovery: The process and outcomes","volume":"9","author":"Calderone","year":"2014","journal-title":"Future Microbiol."},{"key":"10.1016\/j.bioorg.2020.104240_b0050","doi-asserted-by":"crossref","first-page":"594","DOI":"10.3109\/1040841X.2014.974500","article-title":"Novel strategies to fight Candida species infection","volume":"42","author":"Rodrigues","year":"2016","journal-title":"Crit. Rev. Microbiol."},{"key":"10.1016\/j.bioorg.2020.104240_b0055","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1128\/CMR.00029-06","article-title":"Epidemiology of invasive candidiasis: A persistent public health problem","volume":"20","author":"Pfaller","year":"2007","journal-title":"Clin. Microbiol. Rev."},{"key":"10.1016\/j.bioorg.2020.104240_b0060","doi-asserted-by":"crossref","first-page":"1288","DOI":"10.1016\/j.ejmech.2008.08.003","article-title":"2-Acylhydrazino-5-arylpyrrole derivatives: Synthesis and antifungal activity evaluation","volume":"44","author":"Onnis","year":"2009","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0065","doi-asserted-by":"crossref","first-page":"1459","DOI":"10.1086\/516480","article-title":"Epidemiology of Aspergillus Infections in a Large Cohort of Patients Undergoing Bone Marrow Transplantation","volume":"175","author":"Wald","year":"1997","journal-title":"J. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0070","author":"Enoch","year":"2017","journal-title":"Human Fungal Pathogen Identification"},{"key":"10.1016\/j.bioorg.2020.104240_b0075","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1128\/CMR.1.2.187","article-title":"Overview of medically important antifungal azole derivatives","volume":"1","author":"Fromtling","year":"1988","journal-title":"Clin. Microbiol. Rev."},{"key":"10.1016\/j.bioorg.2020.104240_b0080","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1093\/clinids\/2.4.625","article-title":"Chemotherapy for the Systemic Mycoses: The Prelude to Ketoconazole","volume":"2","author":"Utz","year":"2011","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0085","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1371\/journal.ppat.1002870","article-title":"Antifungal Drug Discovery: Something Old and Something New","volume":"8","author":"Butts","year":"2012","journal-title":"PLoS Pathog."},{"key":"10.1016\/j.bioorg.2020.104240_b0090","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1007\/s13225-011-0116-y","article-title":"Fifty years of drug discovery from fungi","volume":"50","author":"Aly","year":"2011","journal-title":"Fungal Divers."},{"key":"10.1016\/j.bioorg.2020.104240_b0095","author":"Mazu","year":"2016","journal-title":"The Mechanistic Targets of Antifungal Agents: An Overview"},{"key":"10.1016\/j.bioorg.2020.104240_b0100","doi-asserted-by":"crossref","unstructured":"D.S. Wishart, Y.D. Feunang, A.C. Guo, E.J. Lo, A. Marcu, J.R. Grant, T. Sajed, D. Johnson, C. Li, Z. Sayeeda, N. Assempour, I. Iynkkaran, Y. Liu, A. MacIejewski, N. Gale, A. Wilson, L. Chin, R. Cummings, Di. Le, A. Pon, C. Knox, M. Wilson, DrugBank 5.0: A major update to the DrugBank database for 2018, Nucleic Acids Res. 46 (2018) D1074\u2013D1082. doi:10.1093\/nar\/gkx1037.","DOI":"10.1093\/nar\/gkx1037"},{"key":"10.1016\/j.bioorg.2020.104240_b0105","doi-asserted-by":"crossref","first-page":"978","DOI":"10.1038\/s41429-018-0100-9","article-title":"Potential targets for the development of new antifungal drugs","volume":"71","author":"Su","year":"2018","journal-title":"J. Antibiot. (Tokyo)"},{"key":"10.1016\/j.bioorg.2020.104240_b0110","doi-asserted-by":"crossref","first-page":"5484","DOI":"10.1021\/acs.jmedchem.7b01413","article-title":"Emerging New Targets for the Treatment of Resistant Fungal Infections","volume":"61","author":"Liu","year":"2018","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0115","doi-asserted-by":"crossref","first-page":"733","DOI":"10.2174\/092986711794480113","article-title":"New Lead Structures in Antifungal Drug Discovery","volume":"18","author":"Sheng","year":"2011","journal-title":"Curr. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0120","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1358\/dot.2015.51.12.2421058","article-title":"Triazole antifungals: A review","volume":"51","author":"Peyton","year":"2015","journal-title":"Drugs of Today."},{"key":"10.1016\/j.bioorg.2020.104240_b0125","doi-asserted-by":"crossref","first-page":"1797","DOI":"10.1517\/13543784.9.8.1797","article-title":"New investigational antifungal agents for treating invasive fungal infections","volume":"9","author":"Hossain","year":"2005","journal-title":"Expert Opin. Invest. Drugs"},{"key":"10.1016\/j.bioorg.2020.104240_b0130","doi-asserted-by":"crossref","unstructured":"M.C.M. Mar\u0131\u0301a Victoria Castelli, Estefan\u0131\u0301a Butassi, F.V.& S.A.Z. Laura A Svetaz, Novel antifungal agents: a patent review (2011 - present), Expert Opin. Ther. Pat. 27 (2014) 415\u2013426. doi:10.1517\/13543776.2014.876993.","DOI":"10.1517\/13543776.2014.876993"},{"key":"10.1016\/j.bioorg.2020.104240_b0135","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1097\/QCO.0b013e32835ebcb7","article-title":"New antifungal antibiotics","volume":"26","author":"Paiva","year":"2013","journal-title":"Curr. Opin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0140","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/S0021-9258(18)72045-0","article-title":"Some biological effects produced by benzimidazole and their reversal by purines","author":"Woolley","year":"1944","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0145","doi-asserted-by":"crossref","first-page":"887","DOI":"10.1016\/0006-2952(74)90220-2","article-title":"Biochemical effects of miconazole on fungi\u2014I","volume":"23","author":"van den Bossche","year":"2002","journal-title":"Biochem. Pharmacol."},{"key":"10.1016\/j.bioorg.2020.104240_b0150","doi-asserted-by":"crossref","first-page":"162","DOI":"10.1111\/j.1439-0507.1958.tb04016.x","article-title":"Pilzhemmende Wirkung eines neuen Benzimidazol-Derivates","volume":"1","author":"Seeliger","year":"1958","journal-title":"Mycoses"},{"key":"10.1016\/j.bioorg.2020.104240_b0155","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/j.1470-9465.2004.00841.x","article-title":"History of the development of azole derivatives","volume":"10","author":"Maertens","year":"2004","journal-title":"Clin. Microbiol. Infect."},{"key":"10.1016\/j.bioorg.2020.104240_b0160","doi-asserted-by":"crossref","first-page":"11242","DOI":"10.1021\/cr5003134","article-title":"Drug strategies targeting CYP51 in neglected tropical diseases","volume":"114","author":"Choi","year":"2014","journal-title":"Chem. Rev."},{"key":"10.1016\/j.bioorg.2020.104240_b0165","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1586\/14787210.2015.1032939","article-title":"Azole antifungals: 35 years of invasive fungal infection management","volume":"13","author":"Allen","year":"2015","journal-title":"Expert Rev. Anti. Infect. Ther."},{"key":"10.1016\/j.bioorg.2020.104240_b0170","doi-asserted-by":"crossref","first-page":"432","DOI":"10.7326\/0003-4819-93-3-432","article-title":"Cardiorespiratory Toxicity Due to Miconazole","volume":"93","author":"Fainstein","year":"2013","journal-title":"Ann. Intern. Med."},{"key":"10.1016\/j.bioorg.2020.104240_b0175","doi-asserted-by":"crossref","first-page":"424","DOI":"10.2165\/00003495-197509060-00003","article-title":"clotrimazole: A Review of its Antifungal Activity and Therapeutic Efficacy","volume":"9","author":"Sawyer","year":"1975","journal-title":"Drugs."},{"key":"10.1016\/j.bioorg.2020.104240_b0180","doi-asserted-by":"crossref","first-page":"113","DOI":"10.2147\/CE.S49629","article-title":"Luliconazole for the treatment of fungal infections: an evidence-based review","author":"Khanna","year":"2014","journal-title":"Core Evid."},{"key":"10.1016\/j.bioorg.2020.104240_b0185","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1021\/jm00194a023","article-title":"Antimycotic imidazoles. Part 4. Synthesis and antifungal activity of ketoconazole, a new potent orally active broad-spectrum antifungal agent","volume":"22","author":"Heeres","year":"1979","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0190","doi-asserted-by":"crossref","first-page":"606","DOI":"10.1093\/clinids\/2.4.606","article-title":"Chronic Mucocutaneous Candidosis and Other Superficial and Systemic Mycoses Successfully Treated with Ketoconazole","volume":"2","author":"Drouhet","year":"2011","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0195","unstructured":"nizoral fda, (n.d.). www.fda.gov\/Drugs\/DrugSafety\/ucm362415.htm."},{"key":"10.1016\/j.bioorg.2020.104240_b0200","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1080\/1120009X.1990.11738981","article-title":"The discovery and profile of fluconazole","volume":"2","author":"Richardson","year":"1990","journal-title":"J. Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0205","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1586\/14787210.2.3.357","article-title":"Fluconazole for the treatment of candidiasis: 15 years experience","volume":"2","author":"Cha","year":"2004","journal-title":"Expert Rev. Anti. Infect. Ther."},{"key":"10.1016\/j.bioorg.2020.104240_b0210","doi-asserted-by":"crossref","first-page":"S276","DOI":"10.1093\/clinids\/12.Supplement_3.S276","article-title":"Fluconazole and other azoles: Translation of in vitro activity to in vivo and clinical efficacy","volume":"12","author":"Troke","year":"1990","journal-title":"Rev. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0215","first-page":"964","article-title":"Management of Invasive Candidal Infections: Results of a Prospective, Randomized, Multicenter Study of Fluconazole Versus Amphotericin B and Review of the Literature","volume":"23","author":"Darouiche","year":"2011","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0220","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1021\/op010064+","article-title":"The discovery and process development of a commercial route to the water soluble prodrug, fosfluconazole","volume":"6","author":"Bentley","year":"2002","journal-title":"Org. Process Res. Dev."},{"key":"10.1016\/j.bioorg.2020.104240_b0225","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1111\/j.1365-2125.2004.02107.x","article-title":"Pharmacokinetics of fosfluconazole and fluconazole following multiple intravenous administration of fosfluconazole in healthy male volunteers","volume":"58","author":"Sobue","year":"2004","journal-title":"Br. J. Clin. Pharmacol."},{"key":"10.1016\/j.bioorg.2020.104240_b0230","unstructured":"D. Abraham, Chemotherapeutic Agents, in: Burger\u2019s Med. Chem. Drug Discov., John Sons, Inc, 2003: pp. 881\u2013910."},{"key":"10.1016\/j.bioorg.2020.104240_b0235","doi-asserted-by":"crossref","first-page":"3782","DOI":"10.1021\/ja00878a046","article-title":"Dimethylsulfonium Methylide, A Reagent for Selective Oxirane Synthesis from Aldehydes and Ketones","volume":"84","author":"Corey","year":"1962","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bioorg.2020.104240_b0240","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1021\/ja01084a033","article-title":"Methylsulfinyl Carbanion (CH 3 -SO-CH 2). Formation and Applications to Organic Synthesis","volume":"87","author":"Corey","year":"1965","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bioorg.2020.104240_b0245","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1021\/ja01062a040","article-title":"Formation and Photochemical Rearrangement of \u03b2\u2019-Ketosulfoxonium Ylides","volume":"86","author":"Corey","year":"1964","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.bioorg.2020.104240_b0250","article-title":"Corey-Chaykovsky epoxidation","author":"Li","year":"2002","journal-title":"Name React."},{"key":"10.1016\/j.bioorg.2020.104240_b0255","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1097\/QCO.0000000000000103","article-title":"Optimizing azole antifungal therapy in the prophylaxis and treatment of fungal infections","volume":"27","author":"Dolton","year":"2014","journal-title":"Curr. Opin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0260","first-page":"561","article-title":"Overview of treatment options for invasive fungal infections","volume":"49","author":"Pound","year":"2011","journal-title":"Med. Mycol."},{"key":"10.1016\/j.bioorg.2020.104240_b0265","doi-asserted-by":"crossref","first-page":"2405","DOI":"10.2165\/11596540-000000000-00000","article-title":"Triazole antifungal agents in invasive fungal infections: A comparative review","volume":"71","author":"Lass-Fl\u00f6rl","year":"2011","journal-title":"Drugs."},{"key":"10.1016\/j.bioorg.2020.104240_b0270","doi-asserted-by":"crossref","unstructured":"S.W. Chapman, W.E. Dismukes, L.A. Proia, R.W. Bradsher, P.G. Pappas, M.G. Threlkeld, C.A. Kauffman, Clinical Practice Guidelines for the Management of Blastomycosis: 2008 Update by the Infectious Diseases Society of America, Clin. Infect. Dis. 46 (2008) 1801\u20131812. doi:10.1086\/588300.","DOI":"10.1086\/588300"},{"key":"10.1016\/j.bioorg.2020.104240_b0275","doi-asserted-by":"crossref","first-page":"1857","DOI":"10.1001\/archinte.1997.00440370097010","article-title":"Analysis Of Compassionate Use Itraconazole Therapy For Invasive Aspergillosis By The Niaid Mycoses Study Group Criteria","volume":"157","author":"Stevens","year":"1997","journal-title":"Arch. Intern. Med."},{"key":"10.1016\/j.bioorg.2020.104240_b0280","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1046\/j.1365-2710.2001.00338.x","article-title":"Itraconazole oral solution and intravenous formulations: a review of pharmacokinetics and pharmacodynamics","volume":"26","author":"Willems","year":"2001","journal-title":"J. Clin. Pharm. Ther."},{"key":"10.1016\/j.bioorg.2020.104240_b0285","doi-asserted-by":"crossref","first-page":"13","DOI":"10.2165\/00003088-198814010-00002","article-title":"Clinical Pharmacokinetics of Ketoconazole","volume":"14","author":"Daneshmend","year":"1988","journal-title":"Clin. Pharmacokinet."},{"key":"10.1016\/j.bioorg.2020.104240_b0290","doi-asserted-by":"crossref","unstructured":"L. Jeu, F.J. Piacenti, A.G. Lyakhovetskiy, H.B. Fung, New bugs Voriconazole, New York. (2003).","DOI":"10.1016\/S0149-2918(03)80126-1"},{"key":"10.1016\/j.bioorg.2020.104240_b0295","doi-asserted-by":"crossref","first-page":"211","DOI":"10.2165\/00003088-200544020-00006","article-title":"Oral Bioavailability of Posaconazole in Fasted Healthy Subjects","volume":"44","author":"Ezzet","year":"2005","journal-title":"Clin. Pharmacokinet."},{"key":"10.1016\/j.bioorg.2020.104240_b0300","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1007\/s15010-017-1042-z","article-title":"Pharmacokinetics of antifungal drugs: practical implications for optimized treatment of patients","volume":"45","author":"Bellmann","year":"2017","journal-title":"Infection"},{"key":"10.1016\/j.bioorg.2020.104240_b0305","doi-asserted-by":"crossref","first-page":"163","DOI":"10.2147\/IDR.S69596","article-title":"Efinaconazole in the treatment of onychomycosis","volume":"8","author":"Lipner","year":"2015","journal-title":"Infect. Drug Resist."},{"key":"10.1016\/j.bioorg.2020.104240_b0310","first-page":"165","article-title":"Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole","volume":"11","author":"Pasqualotto","year":"2010","journal-title":"Curr. Opin. Invest. Drugs"},{"key":"10.1016\/j.bioorg.2020.104240_b0315","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1002\/cpdd.72","article-title":"A randomized, double-blind, multiple-dose, placebo-controlled, dose escalation study with a 3-cohort parallel group design to investigate the tolerability and pharmacokinetics of albaconazole in healthy subjects","volume":"3","author":"Dietz","year":"2014","journal-title":"Clin. Pharmacol. Drug Dev."},{"key":"10.1016\/j.bioorg.2020.104240_b0320","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1128\/AAC.40.1.92","article-title":"Pharmacokinetics and metabolism of genaconazole, a potent antifungal drug, in men","volume":"40","author":"Lin","year":"1996","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0325","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/j.ijantimicag.2012.10.020","article-title":"In vivo pharmacokinetics and in vitro antifungal activity of iodiconazole, a new triazole, determined by microdialysis sampling","volume":"41","author":"Sun","year":"2013","journal-title":"Int. J. Antimicrob. Agents"},{"key":"10.1016\/j.bioorg.2020.104240_b0330","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1128\/AAC.47.2.601-606.2003","article-title":"Efficacy of CS-758, a novel triazole, against experimental fluconazole-resistant oropharyngeal candidiasis in mice","volume":"47","author":"Kamai","year":"2003","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0335","doi-asserted-by":"crossref","first-page":"1577","DOI":"10.4155\/cli.11.137","article-title":"New-generation triazole antifungal drugs: review of the Phase II and III trials","volume":"1","author":"Girmenia","year":"2011","journal-title":"Clin. Investig. (Lond)"},{"key":"10.1016\/j.bioorg.2020.104240_b0340","first-page":"630","article-title":"Voriconazole: A new triazole antifungal agent","volume":"36","author":"Johnson","year":"2003","journal-title":"Rev. ANTI-INFECTIVE AGENTS."},{"key":"10.1016\/j.bioorg.2020.104240_b0345","doi-asserted-by":"crossref","first-page":"2009","DOI":"10.1128\/AAC.00163-06","article-title":"In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts","volume":"50","author":"Sabatelli","year":"2006","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0350","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1016\/j.bmcl.2005.09.031","article-title":"Hydroxylated analogues of the orally active broad spectrum antifungal, Sch 51048 (1), and the discovery of posaconazole [Sch 56592; 2 or (S, S)-5]","volume":"16","author":"Bennett","year":"2006","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0355","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1002\/jms.1341","article-title":"Posaconazole (Noxafil, SCH 56592), a new azole antifungal drug, was a discovery based on the isolation and mass spectral characterization of a circulating metabolite of an earlier lead (SCH 51048)","volume":"43","author":"Nomeir","year":"2008","journal-title":"J. Mass Spectrom."},{"key":"10.1016\/j.bioorg.2020.104240_b0360","doi-asserted-by":"crossref","first-page":"1726","DOI":"10.1086\/504328","article-title":"Safety of Long-Term Oral Posaconazole Use in the Treatment of Refractory Invasive Fungal Infections","volume":"42","author":"Raad","year":"2006","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0365","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1056\/NEJMoa061094","article-title":"Posaconazole vs. Fluconazole or Itraconazole Prophylaxis in Patients with Neutropenia","volume":"356","author":"Cornely","year":"2007","journal-title":"N. Engl. J. Med."},{"key":"10.1016\/j.bioorg.2020.104240_b0370","doi-asserted-by":"crossref","unstructured":"M. Andrew J. Ullmann, M.D., Jeffrey H. Lipton, M.D., David H. Vesole, M.D., Ph.D., Pranatharthi Chandrasekar, M.D., Amelia Langston, M.D., Stefano R. Tarantolo, M.D., Hildegard Greinix, M.D., Wellington Morais de Azevedo, M.D., Ph.D., Vijay Reddy, M.D., Navd, Posaconazole or Fluconazole for Prophylaxis in Severe Graft-versus-Host Disease, N. Engl. J. Med. 356 (2007) 335\u2013347.","DOI":"10.1056\/NEJMoa061098"},{"key":"10.1016\/j.bioorg.2020.104240_b0375","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1086\/508774","article-title":"Treatment of Invasive Aspergillosis with Posaconazole in Patients Who Are Refractory to or Intolerant of Conventional Therapy: An Externally Controlled Trial","volume":"44","author":"Walsh","year":"2007","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0380","doi-asserted-by":"crossref","first-page":"1977","DOI":"10.1007\/s40265-013-0152-x","article-title":"Efinaconazole: First global approval","volume":"73","author":"Patel","year":"2013","journal-title":"Drugs."},{"key":"10.1016\/j.bioorg.2020.104240_b0385","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1128\/AAC.50.1.279-285.2006","article-title":"Single-Ascending-Dose Pharmacokinetics and Safety of the Novel Broad-Spectrum Antifungal Triazole BAL4815 after Intravenous Infusions (50, 100, and 200 Milligrams) and Oral Administrations (100, 200, and 400 Milligrams) of Its Prodrug, BAL8557, in Healthy","volume":"50","author":"Schmitt-hoffmann","year":"2006","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0390","unstructured":"boyd 83, (n.d.). https:\/\/www.aspergillus.org.uk\/content\/bal-4815bal-8557-antifungal-agent."},{"key":"10.1016\/j.bioorg.2020.104240_b0395","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1586\/14787210.2015.990382","article-title":"Isavuconazole, a broad-spectrum triazole for the treatment of systemic fungal diseases","volume":"13","author":"Seyedmousavi","year":"2015","journal-title":"Expert Rev. Anti. Infect. Ther."},{"key":"10.1016\/j.bioorg.2020.104240_b0400","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1177\/1060028015581679","article-title":"Isavuconazole: A New Option for the Management of Invasive Fungal Infections","volume":"49","author":"Pettit","year":"2015","journal-title":"Ann. Pharmacother."},{"key":"10.1016\/j.bioorg.2020.104240_b0405","doi-asserted-by":"crossref","first-page":"E93","DOI":"10.3314\/mmj.16-00006","article-title":"Potential of Ravuconazole and its Prodrugs as the New OralTherapeutics for Onychomycosis","volume":"57","author":"Yamaguchi","year":"2016","journal-title":"Med. Mycol. J."},{"key":"10.1016\/j.bioorg.2020.104240_b0410","doi-asserted-by":"crossref","first-page":"2635","DOI":"10.1128\/AAC.45.9.2635-2637.2001","article-title":"In vitro antifungal activities of the new triazole UR-9825 against clinically important filamentous fungi","volume":"45","author":"Capilla","year":"2001","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0415","unstructured":"clinical trial, (n.d.). https:\/\/clinicaltrials.gov."},{"key":"10.1016\/j.bioorg.2020.104240_b0420","doi-asserted-by":"crossref","first-page":"112463","DOI":"10.1016\/j.ejmech.2020.112463","article-title":"Synthesis of 1, 2, 4-triazole benzoyl arylamine derivatives and their high antifungal activities","volume":"200","author":"Cheng","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0425","doi-asserted-by":"crossref","first-page":"126951","DOI":"10.1016\/j.bmcl.2020.126951","article-title":"Design, synthesis, and structure-activity relationship studies of novel triazole agents with strong antifungal activity against Aspergillus fumigatus","volume":"30","author":"Ding","year":"2020","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0430","doi-asserted-by":"crossref","first-page":"103982","DOI":"10.1016\/j.bioorg.2020.103982","article-title":"Design, synthesis, and in vitro evaluation of novel triazole analogues featuring isoxazole moieties as antifungal agents","volume":"101","author":"Xie","year":"2020","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0435","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1016\/j.ejmech.2017.02.035","article-title":"New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies","volume":"130","author":"Do\u011fan","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0440","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1111\/fcp.12230","article-title":"Targeting CYP51 for drug design by the contributions of molecular modeling","volume":"31","author":"Rabelo","year":"2017","journal-title":"Fundam. Clin. Pharmacol."},{"key":"10.1016\/j.bioorg.2020.104240_b0445","doi-asserted-by":"crossref","first-page":"579","DOI":"10.1016\/j.ejmech.2018.06.022","article-title":"Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungi","volume":"155","author":"Zhang","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0450","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1016\/j.ejmech.2014.05.079","article-title":"Design, synthesis and antifungal activity of novel triazole derivatives containing substituted 1,2,3-triazole-piperdine side chains","volume":"82","author":"Jiang","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0455","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1016\/j.ejmech.2017.03.075","article-title":"Novel alkylated azoles as potent antifungals","volume":"133","author":"Shrestha","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0460","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1016\/j.bmcl.2017.12.040","article-title":"Design, synthesis, and structure-activity relationship studies of novel tetrazole antifungal agents with potent activity, broad antifungal spectrum and high selectivity","volume":"28","author":"Qian","year":"2018","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0465","doi-asserted-by":"crossref","first-page":"2214","DOI":"10.1016\/j.ejmech.2010.01.062","article-title":"Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles","volume":"45","author":"Patel","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0470","doi-asserted-by":"crossref","first-page":"6020","DOI":"10.1016\/j.ejmech.2010.09.070","article-title":"Novel conformationally restricted triazole derivatives with potent antifungal activity","volume":"45","author":"Wang","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0475","doi-asserted-by":"crossref","first-page":"1631","DOI":"10.1039\/C7MD00112F","article-title":"Discovery of potential antifungal triazoles: Design, synthesis, biological evaluation, and preliminary antifungal mechanism exploration","volume":"8","author":"Zhang","year":"2017","journal-title":"Medchemcomm."},{"key":"10.1016\/j.bioorg.2020.104240_b0480","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1016\/j.cclet.2015.04.030","article-title":"Design, synthesis and biological evaluation of novel non-azole derivatives as potential antifungal agents","volume":"26","author":"Tang","year":"2015","journal-title":"Chinese Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0485","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1128\/AAC.01071-18","article-title":"The fungal cyp51 inhibitor vt-1129 is efficacious in an experimental model of cryptococcal meningitis","volume":"62","author":"Wiederhold","year":"2018","journal-title":"Antimicrob. Agents Chemother."},{"issue":"e1\u2013624","key":"10.1016\/j.bioorg.2020.104240_b0490","first-page":"e9","article-title":"A phase 2, randomized, double-blind, placebo-controlled, dose-ranging study to evaluate the efficacy and safety of orally administered VT-1161 in the treatment of recurrent vulvovaginal candidiasis","volume":"624","author":"Brand","year":"2018","journal-title":"Am. J. Obstet. Gynecol."},{"key":"10.1016\/j.bioorg.2020.104240_b0495","doi-asserted-by":"crossref","first-page":"3455","DOI":"10.1016\/j.bmcl.2014.05.068","article-title":"Design and optimization of highly-selective fungal CYP51 inhibitors","volume":"24","author":"Hoekstra","year":"2014","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0500","doi-asserted-by":"crossref","first-page":"3243","DOI":"10.1016\/j.bmcl.2017.06.037","article-title":"Design and optimization of highly-selective, broad spectrum fungal CYP51 inhibitors","volume":"27","author":"Yates","year":"2017","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0505","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1093\/jac\/dkx410","article-title":"Fungal-specific Cyp51 inhibitor VT-1598 demonstrates in vitro activity against Candida and Cryptococcus species, endemic fungi, including Coccidioides species, Aspergillus species and Rhizopus arrhizus","volume":"73","author":"Wiederhold","year":"2018","journal-title":"J. Antimicrob. Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0510","doi-asserted-by":"crossref","first-page":"4530","DOI":"10.1128\/AAC.00349-16","article-title":"The investigational drug VT-1129 is a highly potent inhibitor of Cryptococcus species CYP51 but only weakly inhibits the human enzyme","volume":"60","author":"Warrilow","year":"2016","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0515","doi-asserted-by":"crossref","first-page":"S821","DOI":"10.1016\/j.ajog.2016.09.016","article-title":"15: To evaluate the efficacy and safety of VT-1161, a potent, highly selective inhibitor of fungal CYP51, in treating women with a documented history of recurrent vulvovaginal candidiasis (RVVC)","volume":"215","author":"Brand","year":"2016","journal-title":"Am. J. Obstet. Gynecol."},{"key":"10.1016\/j.bioorg.2020.104240_b0520","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.ejmech.2019.03.023","article-title":"Tetrazole hybrids and their antifungal activities","author":"Wang","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0525","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1016\/j.ijantimicag.2017.09.002","article-title":"The antifungal arsenal: alternative drugs and future targets","volume":"51","author":"Wiederhold","year":"2018","journal-title":"Int. J. Antimicrob. Agents"},{"key":"10.1016\/j.bioorg.2020.104240_b0530","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1128\/AAC.02258-17","article-title":"The novel fungal Cyp51 inhibitor VT-1598 is efficacious in experimental models of central nervous system coccidioidomycosis caused by Coccidioides posadasii and Coccidioides immitis","volume":"62","author":"Wiederhold","year":"2018","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0535","doi-asserted-by":"crossref","DOI":"10.1128\/AAC.02233-18","article-title":"The Fungal Cyp51-Specific Inhibitor VT-1598 Demonstrates In Vitro and In Vivo Activity against Candida auris","author":"Wiederhold","year":"2019","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0540","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1021\/ar7000843","article-title":"Hybrid Molecules with a Dual Mode of Action : Dream or Reality ? \u2020","volume":"41","author":"Meunier","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"10.1016\/j.bioorg.2020.104240_b0545","article-title":"An overview of molecular hybrids in drug discovery","author":"Terms","year":"2016","journal-title":"Expert Opin. Drug Discov."},{"key":"10.1016\/j.bioorg.2020.104240_b0550","doi-asserted-by":"crossref","first-page":"1389","DOI":"10.1007\/s00726-017-2441-2","article-title":"Glycotriazole - peptides derived from the peptide HSP1: synergistic effect of triazole and saccharide rings on the antifungal activity","volume":"49","author":"Martins","year":"2017","journal-title":"Amino Acids"},{"key":"10.1016\/j.bioorg.2020.104240_b0555","doi-asserted-by":"crossref","first-page":"2639","DOI":"10.1002\/cmdc.201402320","article-title":"From Antidiabetic to Antifungal : Discovery of Highly Potent Triazole \u2013 Thiazolidinedione Hybrids as Novel Antifungal Agents","volume":"9","author":"Wu","year":"2014","journal-title":"ChemMedChem"},{"key":"10.1016\/j.bioorg.2020.104240_b0560","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/j.ejmech.2019.03.020","article-title":"Current advances of triazole alcohols derived from fluconazole: Design, in vitro and in silico studies","author":"Emami","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0565","first-page":"51","article-title":"Synthesis of 2 H -1, 2, 3-Triazoles","volume":"1","author":"Belskaya","year":"2015","journal-title":"Top Heterocycl Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0570","doi-asserted-by":"crossref","first-page":"11333","DOI":"10.3390\/molecules190811333","article-title":"Synthesis and Antifungal Activity of Novel Triazole Compounds Containing Piperazine Moiety","volume":"19","author":"Wang","year":"2014","journal-title":"Molecules"},{"key":"10.1016\/j.bioorg.2020.104240_b0575","doi-asserted-by":"crossref","unstructured":"N.D. Thanh, D.S. Hai, V.T. Ngoc Bich, P.T. Thu Hien, N.T. Ky Duyen, N.T. Mai, T.T. Dung, V.N. Toan, H.T. Kim Van, L.H. Dang, D.N. Toan, T.T. Thanh Van, Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene\u2212D-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities, Eur. J. Med. Chem. (2019) 454\u2013471. doi:10.1016\/j.ejmech.2019.01.060.","DOI":"10.1016\/j.ejmech.2019.01.060"},{"key":"10.1016\/j.bioorg.2020.104240_b0580","doi-asserted-by":"crossref","first-page":"2959","DOI":"10.1016\/j.bmcl.2012.02.042","article-title":"Bioorganic & Medicinal Chemistry Letters New triazole derivatives as antifungal agents : Synthesis via click reaction, in vitro evaluation and molecular docking studies","volume":"22","author":"Zou","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0585","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2017.05.001","article-title":"Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans","author":"Fu","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0590","doi-asserted-by":"crossref","first-page":"11178","DOI":"10.1016\/j.tet.2006.09.021","article-title":"Design and synthesis of fluconazole \/ bile acid conjugate using click reaction","volume":"62","author":"Pore","year":"2006","journal-title":"Tetrahedron"},{"key":"10.1016\/j.bioorg.2020.104240_b0595","doi-asserted-by":"crossref","first-page":"3511","DOI":"10.1016\/j.bmc.2019.07.005","article-title":"1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview","volume":"27","author":"Bozorov","year":"2019","journal-title":"Bioorganic Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0600","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1016\/j.ejmech.2015.02.059","article-title":"Biological potential of carbazole derivatives","volume":"94","author":"Gluszynska","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0605","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1016\/j.ejmech.2019.07.003","article-title":"Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles","volume":"179","author":"Elias","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0610","doi-asserted-by":"crossref","unstructured":"G. Han, N. Liu, C. Li, J. Tu, Z. Li, C. Sheng, Discovery of Novel Fungal Lanosterol 14 \u03b1 -Demethylase (CYP51)\/ Histone Deacetylase (HDAC) Dual Inhibitors to treat azole-resistant candidiasis, J. Med. Chem. Discov. Apr (2020). doi:10.1021\/acs.jmedchem.0c00102.","DOI":"10.1021\/acs.jmedchem.0c00102"},{"key":"10.1016\/j.bioorg.2020.104240_b0615","doi-asserted-by":"crossref","DOI":"10.1016\/j.bmcl.2017.10.020","article-title":"Novel potentially antifungal hybrids of 5-flucytosine and fluconazole : Design, synthesis and bioactive evaluation","author":"Fang","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2020.104240_b0620","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1007\/s00239-004-2603-1","article-title":"New aspects on lanosterol 14\u03b1-demethylase and cytochrome P450 evolution: Lanosterol\/cycloartenol diversification and lateral transfer","volume":"59","author":"Re\u017een","year":"2004","journal-title":"J. Mol. Evol."},{"key":"10.1016\/j.bioorg.2020.104240_b0625","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1093\/gbe\/evp036","article-title":"Phylogenomics of Sterol Synthesis: Insights into the Origin, Evolution, and Diversity of a Key Eukaryotic Feature","volume":"1","author":"Desmond","year":"2009","journal-title":"Genome Biol. Evol."},{"key":"10.1016\/j.bioorg.2020.104240_b0630","first-page":"e01134","article-title":"Crystal Structures of Full-Length Lanosterol 14\u03b1-Demethylases of Prominent Fungal Pathogens Candida albicans and Candida glabrata Provide Tools for Antifungal Discovery","volume":"62","author":"Keniya","year":"2018","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0635","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1016\/j.bbagen.2006.07.017","article-title":"Cytochrome P450 systems-biological variations of electron transport chains","volume":"1770","author":"Hannemann","year":"2007","journal-title":"Biochim. Biophys. Acta - Gen. Subj."},{"key":"10.1016\/j.bioorg.2020.104240_b0640","doi-asserted-by":"crossref","first-page":"23916","DOI":"10.1074\/jbc.M115.677310","article-title":"Structure-functional characterization of cytochrome P450 Sterol 14\u03b1-Demethylase (CYP51B) from aspergillus fumigatus and molecular basis for the development of antifungal drugs","volume":"290","author":"Hargrove","year":"2015","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0645","article-title":"Fungal Lanosterol 14\u03b1-demethylase: A target for next-generation antifungal design","author":"Monk","year":"2019","journal-title":"Biochim. Biophys. Acta - Proteins Proteomics."},{"key":"10.1016\/j.bioorg.2020.104240_b0650","article-title":"The fungal CYP51s: Their functions, structures, related drug resistance, and inhibitors","volume":"10","author":"Zhang","year":"2019","journal-title":"Front. Microbiol."},{"key":"10.1016\/j.bioorg.2020.104240_b0655","doi-asserted-by":"crossref","unstructured":"F.V. Galina. Lepesheva, Tatiana Y. Hargrove1, Girish Rachakonda, Zdzislaw Wawrzak, S\u00e9bastien Pomel, Sandrine Cojean, Pius N. Nde, W. David Nes, Charles W. Locuson, M. Wade Calcutt, Michael R. Waterman, J. Scott Daniels, Philippe M. Loiseau, VFV as a new effective CYP51 structure-derived drug candidate for Chagas disease and visceral leishmaniasis, J. Infect. Dis. April 15 (2015) 1\u201325. doi:10.1093\/infdis\/jiv228.","DOI":"10.1093\/infdis\/jiv228"},{"key":"10.1016\/j.bioorg.2020.104240_b0660","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1093\/infdis\/jit042","article-title":"VNI cures acute and chronic experimental chagas disease","volume":"208","author":"Villalta","year":"2013","journal-title":"J. Infect. Dis."},{"key":"10.1016\/j.bioorg.2020.104240_b0665","doi-asserted-by":"crossref","first-page":"1773","DOI":"10.1074\/jbc.M109.067470","article-title":"Crystal structures of Trypanosoma brucei sterol 14\u03b1-demethylase and implications for selective treatment of human infections","volume":"285","author":"Lepesheva","year":"2010","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0670","doi-asserted-by":"crossref","first-page":"6728","DOI":"10.1074\/jbc.M117.778308","article-title":"Structural analyses of Candida albicans sterol 14\u03b1-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis","volume":"292","author":"Hargrove","year":"2017","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0675","first-page":"88","article-title":"Structural basis for conservation in the CYP51 family","volume":"2011","author":"Lepesheva","year":"1814","journal-title":"Biochim. Biophys. Acta - Proteins Proteomics."},{"key":"10.1016\/j.bioorg.2020.104240_b0680","doi-asserted-by":"crossref","first-page":"4982","DOI":"10.1128\/AAC.00925-15","article-title":"Structural insights into binding of the antifungal drug fluconazole to Saccharomyces cerevisiae lanosterol 14\u03b1-demethylase","volume":"59","author":"Sagatova","year":"2015","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0685","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1007\/s00894-009-0527-9","article-title":"Evolutionary trace analysis of CYP51 family: Implication for site-directed mutagenesis and novel antifungal drug design","volume":"16","author":"Sheng","year":"2010","journal-title":"J. Mol. Model."},{"key":"10.1016\/j.bioorg.2020.104240_b0690","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1128\/AAC.02114-18","article-title":"Azole resistance reduces susceptibility to the tetrazole antifungal VT-1161","volume":"63","author":"Monk","year":"2019","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0695","unstructured":"5ul0 116, (n.d.). https:\/\/www.rcsb.org\/structure\/5ul0."},{"key":"10.1016\/j.bioorg.2020.104240_b0700","doi-asserted-by":"crossref","first-page":"3865","DOI":"10.1073\/pnas.1324245111","article-title":"Architecture of a single membrane spanning cytochrome P450 suggests constraints that orient the catalytic domain relative to a bilayer","volume":"111","author":"Monk","year":"2014","journal-title":"Proc. Natl. Acad. Sci."},{"key":"10.1016\/j.bioorg.2020.104240_b0705","doi-asserted-by":"crossref","first-page":"5679","DOI":"10.1021\/acs.jmedchem.8b00641","article-title":"Sterol 14\u03b1-Demethylase Structure-Based Design of VNI ((R)- N-(1-(2,4-Dichlorophenyl)-2-(1 H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide)) Derivatives to Target Fungal Infections: Synthesis, Biological Evaluation, and Crystallographic A","volume":"61","author":"Friggeri","year":"2018","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0710","doi-asserted-by":"crossref","DOI":"10.1128\/AAC.00570-17","article-title":"Crystal structure of the new investigational drug candidate VT-1598 in complex with Aspergillus fumigatus sterol 14\u03b1-demethylase provides insights into its broad-spectrum Antifungal Activity","volume":"61","author":"Hargrove","year":"2017","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.bioorg.2020.104240_b0715","doi-asserted-by":"crossref","unstructured":"D.W. Denning, M.J. Bromley, How to bolster the antifungal pipeline, Science (80-.). 347 (2015) 1414\u20131416. doi:10.1126\/science.aaa6097.","DOI":"10.1126\/science.aaa6097"},{"key":"10.1016\/j.bioorg.2020.104240_b0720","first-page":"247","article-title":"Inhibition of Cytochrome P450 Enzymes, Cytochrome P450 Struct","author":"Correia","year":"2005","journal-title":"Mech. Biochem."},{"key":"10.1016\/j.bioorg.2020.104240_b0725","doi-asserted-by":"crossref","first-page":"2493","DOI":"10.1021\/jm990589g","article-title":"A three-dimensional model of lanosterol 14\u03b1-demethylase of Candida albicans and its interaction with azole antifungals","volume":"43","author":"Ji","year":"2000","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0730","doi-asserted-by":"crossref","unstructured":"K. Tasaka, A.; Kitazaki, T.; Tsuchimori, N.; Matsushita, Y.; Hayashi, R.; Okonogi, K.; Itoh, Optically active antifungal azoles. VII. Synthesis and antifungal activity of stereoisomers of 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol- 1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)- 1,2,4-triazolone (TAK-, Chem. Pharm. Bull. 45 (1997) 321\u2013326. doi:10.1248\/cpb.45.321.","DOI":"10.1248\/cpb.45.321"},{"key":"10.1016\/j.bioorg.2020.104240_b0735","doi-asserted-by":"crossref","first-page":"2818","DOI":"10.1021\/jm00093a015","article-title":"Stereoisomers of Ketoconazole: Preparation and Biological Activity","volume":"35","author":"Rotstein","year":"1992","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0740","first-page":"no-no","article-title":"ChemInform Abstract: New Azole Antifungals. Part 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol","volume":"29","author":"Bartroli","year":"2010","journal-title":"ChemInform."},{"key":"10.1016\/j.bioorg.2020.104240_b0745","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1007\/BF00125508","article-title":"Antifungal triazole alcohols: A comparative analysis of structure-activity, structure-teratogenicity and structure-therapeutic index relationships using the Multiple Computer-Automated Structure Evaluation (Multi-CASE) methodology","volume":"7","author":"Klopman","year":"1993","journal-title":"J. Comput. Aided Mol. Des."},{"key":"10.1016\/j.bioorg.2020.104240_b0750","doi-asserted-by":"crossref","unstructured":"J. Bartroli, E. Turmo, M. Alguer\u00f3, E. Boncompte, M.L. Vericat, J. GARCIA-RAFANELL, J. FORN, Synthesis and antifungal activity of new azole derivatives containing an N-acylmorpholine ring, J. Med. Chem. 38 (1995) 3918\u20133932. doi:10.1021\/jm00020a005.","DOI":"10.1021\/jm00020a005"},{"key":"10.1016\/j.bioorg.2020.104240_b0755","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.ejmech.2016.05.032","article-title":"Discovery of in vitro antitubercular agents through in silico ligand-based approaches","volume":"121","author":"De Vita","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0760","doi-asserted-by":"crossref","first-page":"6704","DOI":"10.1021\/jm500739f","article-title":"Structural basis for rational design of inhibitors targeting Trypanosoma cruzi Sterol 14\u03b1-demethylase: Two regions of the enzyme molecule potentiate its inhibition","volume":"57","author":"Friggeri","year":"2014","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0765","doi-asserted-by":"crossref","first-page":"3068","DOI":"10.1073\/pnas.061562898","article-title":"Crystal structure of cytochrome P450 14 -sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors","volume":"98","author":"Podust","year":"2002","journal-title":"Proc. Natl. Acad. Sci."},{"key":"10.1016\/j.bioorg.2020.104240_b0770","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1080\/14756360600700640","article-title":"Synthesis and antifungal activity of new thienyl and aryl conazoles","volume":"21","author":"Chevreuil","year":"2006","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0775","doi-asserted-by":"crossref","first-page":"2512","DOI":"10.1021\/jm051211n","article-title":"Structure-based optimization of azole antifungal agents by CoMFA, CoMSIA, and molecular docking","volume":"49","author":"Sheng","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2020.104240_b0780","doi-asserted-by":"crossref","unstructured":"J. Bartroli, E. Turmo, M. Alguer\u00f3, E. Boncompte, M.L. Vericat, L. Conte, J. Ramis, M. Merlos, New Azole Antifungals. 3. Synthesis and Antifungal Activity of 3-Substituted-4(3H)-quinazolinones, J. Med. Chem. 41 (1998) 1869\u20131882.","DOI":"10.1021\/jm9707277"},{"key":"10.1016\/j.bioorg.2020.104240_b0785","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.mib.2018.02.005","article-title":"Antifungal drug resistance: evolution, mechanisms and impact","volume":"45","author":"Revie","year":"2018","journal-title":"Curr. Opin. Microbiol."},{"key":"10.1016\/j.bioorg.2020.104240_b0790","doi-asserted-by":"crossref","first-page":"802","DOI":"10.1016\/j.drudis.2018.01.003","article-title":"Targeting Candida spp. to develop antifungal agents","volume":"23","author":"Salci","year":"2018","journal-title":"Drug Discov. Today."},{"key":"10.1016\/j.bioorg.2020.104240_b0795","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1111\/lam.12820","article-title":"Antifungals discovery: an insight into new strategies to combat antifungal resistance","volume":"66","author":"Fuentefria","year":"2018","journal-title":"Lett. Appl. Microbiol."},{"key":"10.1016\/j.bioorg.2020.104240_b0800","doi-asserted-by":"crossref","DOI":"10.1155\/2017\/9870679","article-title":"Antifungal Resistance, Metabolic Routes as Drug Targets, and New Antifungal Agents: An Overview about Endemic Dimorphic Fungi","volume":"2017","author":"Parente-Rocha","year":"2017","journal-title":"Mediators Inflamm."}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206820315376?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206820315376?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,11,19]],"date-time":"2025-11-19T15:28:33Z","timestamp":1763566113000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206820315376"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11]]},"references-count":160,"alternative-id":["S0045206820315376"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.104240","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2020,11]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"History of the development of antifungal azoles: A review on structures, SAR, and mechanism of action","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2020.104240","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"104240"}}