{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,11]],"date-time":"2026-05-11T22:50:14Z","timestamp":1778539814107,"version":"3.51.4"},"reference-count":45,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2019,10,1]],"date-time":"2019-10-01T00:00:00Z","timestamp":1569888000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2019,10,1]],"date-time":"2019-10-01T00:00:00Z","timestamp":1569888000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"DOI":"10.13039\/501100003091","name":"Shandong Province","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003091","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2019,10]]},"DOI":"10.1016\/j.ejmech.2019.07.022","type":"journal-article","created":{"date-parts":[[2019,7,11]],"date-time":"2019-07-11T11:13:48Z","timestamp":1562843628000},"page":"321-339","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":17,"special_numbering":"C","title":["Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1, 2, 3-triazole side chain"],"prefix":"10.1016","volume":"180","author":[{"given":"Yinhui","family":"Qin","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuetai","family":"Teng","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ruixin","family":"Ma","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fangchao","family":"Bi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhiyang","family":"Liu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Panpan","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9961-9046","authenticated-orcid":false,"given":"Shutao","family":"Ma","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2019.07.022_bib1","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1517\/14656566.3.8.1131","article-title":"The evolution and role of macrolides in infectious diseases","volume":"3","author":"Blondeau","year":"2002","journal-title":"Expert Opin. Pharmacother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib2","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1517\/13543784.11.2.189","article-title":"The macrolides","volume":"11","author":"Blondeau","year":"2002","journal-title":"Expert Opin. Investig. Drugs"},{"key":"10.1016\/j.ejmech.2019.07.022_bib3","first-page":"281","article-title":"Ilotycin, a new antibiotic","volume":"2","author":"McGuire","year":"1952","journal-title":"Antibiot. Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib4","doi-asserted-by":"crossref","first-page":"362","DOI":"10.1007\/BF02137246","article-title":"Acid degradation of erythromycin A and erythromycin B","volume":"27","author":"Kurath","year":"1971","journal-title":"Experientia"},{"key":"10.1016\/j.ejmech.2019.07.022_bib5","doi-asserted-by":"crossref","first-page":"187","DOI":"10.7164\/antibiotics.37.187","article-title":"Chemical modification of erythromycins. I. Synthesis and antibacterial activity of 6-O-methylerythromycins A","volume":"37","author":"Morimoto","year":"1984","journal-title":"J.\u00a0Antibiot. (Tokyo)"},{"key":"10.1016\/j.ejmech.2019.07.022_bib6","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1248\/yakushi1947.112.9_593","article-title":"Research and development of clarithromycin","volume":"112","author":"Omura","year":"1992","journal-title":"Yakugaku Zasshi"},{"key":"10.1016\/j.ejmech.2019.07.022_bib7","doi-asserted-by":"crossref","first-page":"1881","DOI":"10.1039\/P19860001881","article-title":"Erythromycin series. Part 11. Ring expansion of erythromycin A oxime by the Beckmann rearrangement","volume":"11","author":"Djokic","year":"1986","journal-title":"J.\u00a0Chem. Soc., Perkin Trans. 1: Org. Bio-Org. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib8","doi-asserted-by":"crossref","first-page":"1948","DOI":"10.1128\/AAC.31.12.1948","article-title":"Pharmacokinetic and in\u00a0vivo studies with azithromycin (CP-62,993), a new macrolide with an extended half-life and excellent tissue distribution","volume":"31","author":"Girard","year":"1987","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib9","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1007\/BF01975847","article-title":"Comparison of three-day and five-day courses of azithromycin in the treatment of atypical pneumonia","volume":"10","author":"Schonwald","year":"1991","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"10.1016\/j.ejmech.2019.07.022_bib10","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1128\/AAC.39.3.577","article-title":"Erythromycin resistance by ribosome modification","volume":"39","author":"Weisblum","year":"1995","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib11","doi-asserted-by":"crossref","first-page":"2823","DOI":"10.1128\/AAC.43.12.2823","article-title":"Nomenclature for macrolide and macrolide-lincosamide-streptogramin B resistance determinants","volume":"43","author":"Roberts","year":"1999","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib12","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1093\/jac\/dkf806","article-title":"Molecular characterization of macrolide resistance mechanisms among Streptococcus pneumoniae and Streptococcus pyogenes isolated from the PROTEKT 1999-2000 study","volume":"50","author":"Farrell","year":"2002","journal-title":"J.\u00a0Antimicrob. Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib13","doi-asserted-by":"crossref","first-page":"961","DOI":"10.2174\/1568026033452140","article-title":"Recent developments in macrolide antimicrobial research","volume":"3","author":"Asaka","year":"2003","journal-title":"Curr. Top. Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib14","doi-asserted-by":"crossref","first-page":"3075","DOI":"10.1016\/S0960-894X(99)00534-X","article-title":"Synthesis and antibacterial activity of HMR 3647, a new ketolide highly potent against erythromycin-resistant and susceptible pathogens","volume":"9","author":"Denis","year":"1999","journal-title":"Bioorg. Med. Chem. Lett"},{"key":"10.1016\/j.ejmech.2019.07.022_bib15","doi-asserted-by":"crossref","first-page":"1045","DOI":"10.1021\/jm990618n","article-title":"Design, synthesis, and antimicrobial activity of 6-O-substituted ketolides active against resistant respiratory tract pathogens","volume":"43","author":"Or","year":"2000","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib16","doi-asserted-by":"crossref","first-page":"3136","DOI":"10.1021\/jacs.5b13008","article-title":"Ribosome-templated azide-alkyne cycloadditions: synthesis of potent macrolide antibiotics by in situ click chemistry","volume":"138","author":"Glassford","year":"2016","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.ejmech.2019.07.022_bib17","doi-asserted-by":"crossref","first-page":"1737","DOI":"10.1007\/s40265-016-0667-z","article-title":"Solithromycin: a novel fluoroketolide for the treatment of community-acquired bacterial pneumonia","volume":"76","author":"Zhanel","year":"2016","journal-title":"Drugs"},{"issue":"Suppl S1","key":"10.1016\/j.ejmech.2019.07.022_bib18","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1093\/jac\/dkf808","article-title":"Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in\u00a0vitro activity of the ketolide, telithromycin","volume":"50","author":"Felmingham","year":"2002","journal-title":"J.\u00a0Antimicrob. Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib19","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.ijantimicag.2010.08.021","article-title":"Antimicrobial characterisation of solithromycin (CEM-101), a novel fluoroketolide: activity against staphylococci and enterococci","volume":"37","author":"Putnam","year":"2011","journal-title":"Int. J. Antimicrob. Agents"},{"key":"10.1016\/j.ejmech.2019.07.022_bib20","doi-asserted-by":"crossref","first-page":"4276","DOI":"10.1128\/JB.185.14.4276-4279.2003","article-title":"Structural insight into the antibiotic action of telithromycin against resistant mutants","volume":"185","author":"Berisio","year":"2003","journal-title":"J.\u00a0Bacteriol."},{"key":"10.1016\/j.ejmech.2019.07.022_bib21","doi-asserted-by":"crossref","first-page":"4961","DOI":"10.1128\/AAC.00860-10","article-title":"Binding and action of CEM-101, a new fluoroketolide antibiotic that inhibits protein synthesis","volume":"54","author":"Llano-Sotelo","year":"2010","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2019.07.022_bib22","doi-asserted-by":"crossref","first-page":"17158","DOI":"10.1073\/pnas.1008685107","article-title":"Revisiting the structures of several antibiotics bound to the bacterial ribosome","volume":"107","author":"Bulkley","year":"2010","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"10.1016\/j.ejmech.2019.07.022_bib23","doi-asserted-by":"crossref","first-page":"E5805","DOI":"10.1073\/pnas.1517952112","article-title":"Structural insights into species-specific features of the ribosome from the pathogen Staphylococcus aureus","volume":"112","author":"Eyal","year":"2015","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"10.1016\/j.ejmech.2019.07.022_bib24","doi-asserted-by":"crossref","first-page":"4137","DOI":"10.1021\/jm0102349","article-title":"Novel erythromycin derivatives with aryl groups tethered to the C-6 position are potent protein synthesis inhibitors and active against multidrug-resistant respiratory pathogens","volume":"44","author":"Ma","year":"2001","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib25","doi-asserted-by":"crossref","first-page":"1795","DOI":"10.1021\/jm025580k","article-title":"Synthesis and antibacterial activity of 6-O-arylbutynyl ketolides with improved activity against some key erythromycin-resistant pathogens","volume":"46","author":"Keyes","year":"2003","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib26","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1038\/nature17967","article-title":"A\u00a0platform for the discovery of new macrolide antibiotics","volume":"533","author":"Seiple","year":"2016","journal-title":"Nature"},{"key":"10.1016\/j.ejmech.2019.07.022_bib27","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1038\/ja.2005.19","article-title":"15-amido erythromycins: synthesis and in\u00a0vitro activity of a new class of macrolide antibiotics","volume":"58","author":"Shaw","year":"2005","journal-title":"J.\u00a0Antibiot. (Tokyo)"},{"key":"10.1016\/j.ejmech.2019.07.022_bib28","doi-asserted-by":"crossref","first-page":"392","DOI":"10.1038\/ja.2006.56","article-title":"Preparation of erythromycin analogs having functional groups at C-15","volume":"59","author":"Ashley","year":"2006","journal-title":"J.\u00a0Antibiot. (Tokyo)"},{"key":"10.1016\/j.ejmech.2019.07.022_bib29","doi-asserted-by":"crossref","first-page":"10129","DOI":"10.1016\/j.bmc.2008.09.054","article-title":"Novel azalides derived from 16-membered macrolides. Part II: isolation of the linear 9-formylcarboxylic acid and its sequential macrocyclization with an amino alcohol or an azidoamine","volume":"16","author":"Miura","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib30","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1021\/ml100252s","article-title":"Synthesis and antibacterial activity of a novel class of 15-membered macrolide antibiotics, \"11a-azalides\"","volume":"2","author":"Sugimoto","year":"2011","journal-title":"ACS Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2019.07.022_bib31","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1016\/j.mib.2008.08.003","article-title":"Macrolide myths","volume":"11","author":"Mankin","year":"2008","journal-title":"Curr. Opin. Microbiol."},{"key":"10.1016\/j.ejmech.2019.07.022_bib32","doi-asserted-by":"crossref","first-page":"814","DOI":"10.1038\/35101544","article-title":"Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria","volume":"413","author":"Schlunzen","year":"2001","journal-title":"Nature"},{"key":"10.1016\/j.ejmech.2019.07.022_bib33","doi-asserted-by":"crossref","first-page":"7033","DOI":"10.1016\/S0040-4020(03)00817-2","article-title":"Synthetic studies of erythromycin derivatives: 6-O-methylation of (9S)-12, 21-anhydro-9-dihydroerythromycin A derivatives","volume":"59","author":"Chen","year":"2003","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2019.07.022_bib34","doi-asserted-by":"crossref","first-page":"5787","DOI":"10.1016\/j.bmc.2012.08.007","article-title":"Synthesis and structure-activity relationship of a novel class of 15-membered macrolide antibiotics known as '11a-azalides'","volume":"20","author":"Sugimoto","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib35","doi-asserted-by":"crossref","first-page":"3849","DOI":"10.1021\/jo960057x","article-title":"Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures(1)","volume":"61","author":"Abdel-Magid","year":"1996","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib36","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1021\/jo00288a004","article-title":"Chiral synthesis of polyketide-derived natural products. 27. Stereoselective synthesis of erythronolide A via an extremely efficient macrolactonization by the modified Yamaguchi method","volume":"55","author":"Hikota","year":"1990","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib37","doi-asserted-by":"crossref","first-page":"45","DOI":"10.3998\/ark.5550190.0013.605","article-title":"An expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones: a short and efficient synthesis of linezolid","volume":"6","author":"Tammana","year":"2012","journal-title":"ARKIVOC (Gainesville, FL, United States)"},{"key":"10.1016\/j.ejmech.2019.07.022_bib38","doi-asserted-by":"crossref","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A\u00a0stepwise huisgen cycloaddition process: copper (I) - catalyzed regioselective \u201cligation\u201d of azides and terminal alkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1016\/j.ejmech.2019.07.022_bib39","doi-asserted-by":"crossref","first-page":"6511","DOI":"10.1016\/j.tetlet.2013.09.084","article-title":"Concise synthesis of (+)-serinolamide A","volume":"54","author":"Gao","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2019.07.022_bib40","doi-asserted-by":"crossref","first-page":"5838","DOI":"10.1021\/ic302798u","article-title":"Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(II) ions: thermodynamic and kinetic evaluations","volume":"52","author":"Simmons","year":"2013","journal-title":"Inorg. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib41","doi-asserted-by":"crossref","first-page":"2743","DOI":"10.1039\/C5SC04144A","article-title":"Stereoselective synthesis of protected L- and D-dideoxysugars and analogues via Prins cyclisations","volume":"7","author":"Beattie","year":"2016","journal-title":"Chem. Sci."},{"key":"10.1016\/j.ejmech.2019.07.022_bib42","doi-asserted-by":"crossref","first-page":"2323","DOI":"10.1039\/C5GC02880A","article-title":"An efficient synthesis of N-nitrosamines under solvent, metal and acid free conditions using tert-butyl nitrite","volume":"18","author":"Chaudhary","year":"2016","journal-title":"Green Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib43","doi-asserted-by":"crossref","first-page":"1296","DOI":"10.1021\/jo00003a067","article-title":"A\u00a0new aspect of the high-field NMR application of Mosher's method. The absolute configuration of marine triterpene sipholenol A","volume":"56","author":"Ohtani","year":"1991","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2019.07.022_bib44","doi-asserted-by":"crossref","first-page":"3147","DOI":"10.1016\/S0040-4039(00)99187-1","article-title":"Absolute configurations of marine diterpenes possessing a xenicane skeleton. An application of an advanced Mosher's method","volume":"30","author":"Ohtani","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2019.07.022_bib45","series-title":"Methods for Dilution Antimicrobial Sucseptibility Tests for Bacteria that Grow Aerobically","first-page":"M07","author":"Wikler","year":"2009"}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523419306439?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523419306439?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T13:58:09Z","timestamp":1759327089000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523419306439"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,10]]},"references-count":45,"alternative-id":["S0223523419306439"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2019.07.022","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2019,10]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1, 2, 3-triazole side chain","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2019.07.022","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2019 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}