{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T15:09:10Z","timestamp":1764774550118,"version":"3.46.0"},"reference-count":73,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T00:00:00Z","timestamp":1764720000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Scientific Foundation","doi-asserted-by":"publisher","award":["23-14-00106"],"award-info":[{"award-number":["23-14-00106"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The problem of antibiotic resistance is one of the challenges that science and medicine face in the 21st century. Nucleoside analogs have already proven as antiviral and antitumor agents, and, currently, there are more and more reports on their antibacterial and antifungal activity. The substitution of an oxygen atom by a sulfur one leads to the emergence of unique properties. Here, we report the synthesis of eight new 4-thioanalogs of 5-substituted (5-alkyloxymethyl and 5-alkyltriazolylmethyl) derivatives of 2\u2032-deoxyuridine and uridine, which were active against Mycobacterium tuberculosis and Gram-positive bacteria. The novel sulfur-containing nucleosides were synthesized via activation of the pyrimidine C4 position, followed by condensation with thioacetic acid and deblocking. To increase the solubility, oligoglycol carbonate depot forms were obtained via activation of the 3\u2032-hydroxyl group using N,N\u2019-carbonyldiimidazole and condensation with triethylene glycol. The highest inhibitory activity was demonstrated by 3\u2032-triethylene glycol depot forms of 4-thio-5-undecyl- and 5-dodecyloxymethyl-2\u2032-deoxyuridine (4a,b) against two strains of M. smegmatis. The most promising compounds were 5-[4-decyl-(1,2,3-triazol-1-yl)methyl]-4-thio-2\u2032-deoxy- and ribouridine (3c,g) and 5-undecyloxymethyl 4-thiouridine (3e) active toward clinical M. intracellulare isolates. Overall, novel sulfur-containing nucleoside analogs were low toxic, demonstrated better inhibitory activity compared to their C4-oxo ones, and, thus, are promising compounds for the development of new antibacterial agents.<\/jats:p>","DOI":"10.3390\/ijms262311712","type":"journal-article","created":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T15:02:48Z","timestamp":1764774168000},"page":"11712","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["5-Substituted 4-Thiouridines, 4-Thio-2\u2032-deoxyuridines and Their Oligoglycol Carbonate Prodrugs as Promising Antimicrobial Agents"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2438-1146","authenticated-orcid":false,"given":"Dmitry A.","family":"Makarov","sequence":"first","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0462-8930","authenticated-orcid":false,"given":"Maxim V.","family":"Jasko","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2885-8442","authenticated-orcid":false,"given":"Sergey D.","family":"Negrya","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9849-0447","authenticated-orcid":false,"given":"Inna L.","family":"Karpenko","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-7587-7526","authenticated-orcid":false,"given":"Elizabeth V.","family":"Urbina","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1247-9517","authenticated-orcid":false,"given":"Vladimir O.","family":"Chekhov","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3131-1031","authenticated-orcid":false,"given":"Olga V.","family":"Efremenkova","sequence":"additional","affiliation":[{"name":"Gause Institute of New Antibiotics, 119021 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9077-1965","authenticated-orcid":false,"given":"Byazilya F.","family":"Vasilyeva","sequence":"additional","affiliation":[{"name":"Gause Institute of New Antibiotics, 119021 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2040-0904","authenticated-orcid":false,"given":"Danila V.","family":"Zimenkov","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7935-4316","authenticated-orcid":false,"given":"Anastasia I.","family":"Ushtanit","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7443-6961","authenticated-orcid":false,"given":"Sergey N.","family":"Kochetkov","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Liudmila A.","family":"Alexandrova","sequence":"additional","affiliation":[{"name":"Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Aminov, R.I. (2010). A Brief History of the Antibiotic Era: Lessons Learned and Challenges for the Future. Front. Microbiol., 1.","DOI":"10.3389\/fmicb.2010.00134"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1038\/s41429-023-00629-8","article-title":"Antibiotics in the Clinical Pipeline as of December 2022","volume":"76","author":"Butler","year":"2023","journal-title":"J. Antibiot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"eabo7793","DOI":"10.1126\/scitranslmed.abo7793","article-title":"The Past, Present, and Future of Antibiotics","volume":"14","author":"Cook","year":"2022","journal-title":"Sci. Transl. Med."},{"key":"ref_4","first-page":"277","article-title":"The Antibiotic Resistance Crisis: Part 1: Causes and Threats","volume":"40","author":"Ventola","year":"2015","journal-title":"Pharm. Ther."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Sengupta, S., Chattopadhyay, M.K., and Grossart, H.-P. (2013). The Multifaceted Roles of Antibiotics and Antibiotic Resistance in Nature. Front. Microbiol., 4.","DOI":"10.3389\/fmicb.2013.00047"},{"key":"ref_6","unstructured":"World Health Organization (2025). Global Antibiotic Resistance Surveillance Report 2025, World Health Organization."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1483","DOI":"10.1021\/acsinfecdis.4c00115","article-title":"Navigating Antibacterial Frontiers: A Panoramic Exploration of Antibacterial Landscapes, Resistance Mechanisms, and Emerging Therapeutic Strategies","volume":"10","author":"Ralhan","year":"2024","journal-title":"ACS Infect. Dis."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Santajit, S., and Indrawattana, N. (2016). Mechanisms of Antimicrobial Resistance in ESKAPE Pathogens. Biomed Res. Int., 2016.","DOI":"10.1155\/2016\/2475067"},{"key":"ref_9","first-page":"1","article-title":"Antimicrobial-Resistant Pathogens Associated with Adult Healthcare-Associated Infections: Summary of Data Reported to the National Healthcare Safety Network, 2015\u20132017","volume":"41","author":"Abner","year":"2020","journal-title":"Infect. Control Hosp. Epidemiol."},{"key":"ref_10","unstructured":"World Health Organization (2025, October 27). Global Tuberculosis Report. Available online: www.who.int\/health-topics\/tuberculosis."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1002\/med.21602","article-title":"An Overview of New Antitubercular Drugs, Drug Candidates, and Their Targets","volume":"40","author":"Bahuguna","year":"2020","journal-title":"Med. Res. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1370","DOI":"10.5588\/ijtld.14.0120","article-title":"The Epidemiologic Relationship between Tuberculosis and Non-Tuberculous Mycobacterial Disease: A Systematic Review","volume":"18","author":"Brode","year":"2014","journal-title":"Int. J. Tuberc. Lung Dis."},{"key":"ref_13","unstructured":"World Health Organization (2023). Global Tuberculosis Report 2023, World Health Organization."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.ijid.2022.10.013","article-title":"Global Trends of Pulmonary Infections with Nontuberculous Mycobacteria: A Systematic Review","volume":"125","author":"Dahl","year":"2022","journal-title":"Int. J. Infect. Dis."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"139796","DOI":"10.1016\/j.scitotenv.2020.139796","article-title":"Influence of Climate Variables on the Rising Incidence of Nontuberculous Mycobacterial (NTM) Infections in Queensland, Australia 2001\u20132016","volume":"740","author":"Thomson","year":"2020","journal-title":"Sci. Total Environ."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Behra, P.R.K., Pettersson, B.M.F., Ramesh, M., Das, S., Dasgupta, S., and Kirsebom, L.A. (2022). Comparative Genome Analysis of Mycobacteria Focusing on TRNA and Non-Coding RNA. BMC Genom., 23.","DOI":"10.1186\/s12864-022-08927-5"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"100017","DOI":"10.1016\/j.clinme.2024.100017","article-title":"Non-Tuberculous Mycobacterial Pulmonary Disease (NTM-PD): Epidemiology, Diagnosis and Multidisciplinary Management","volume":"24","author":"Kumar","year":"2024","journal-title":"Clin. Med."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1136\/thoraxjnl-2014-206470","article-title":"Increased Risk of Mycobacterial Infections Associated with Anti-Rheumatic Medications","volume":"70","author":"Brode","year":"2015","journal-title":"Thorax"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"968","DOI":"10.1016\/S1473-3099(15)00089-4","article-title":"Host Susceptibility to Non-Tuberculous Mycobacterial Infections","volume":"15","author":"Wu","year":"2015","journal-title":"Lancet Infect. Dis."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"e000498","DOI":"10.1136\/bmjresp-2019-000498","article-title":"Non-Tuberculous Mycobacterial Lung Disease in Patients with Bronchiectasis: Perceived Risk, Severity and Guideline Adherence in a European Physician Survey","volume":"7","author":"Wagner","year":"2020","journal-title":"BMJ open Respir. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"00336-2022","DOI":"10.1183\/23120541.00336-2022","article-title":"Global Burden of Nontuberculous Mycobacteria in the Cystic Fibrosis Population: A Systematic Review and Meta-Analysis","volume":"9","author":"Prieto","year":"2023","journal-title":"ERJ open Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1579","DOI":"10.7754\/Clin.Lab.2024.240315","article-title":"Multiple Postoperative Lung Infections after Thymoma Surgery Diagnosed as Nontuberculous Mycobacterial Infection","volume":"70","author":"Nie","year":"2024","journal-title":"Clin. Lab."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"107259","DOI":"10.1016\/j.ijid.2024.107259","article-title":"Demographic and Clinical Features of Nontuberculous Mycobacteria Infection Resulting from Cosmetic Procedures: A Systematic Review","volume":"149","author":"Ma","year":"2024","journal-title":"Int. J. Infect. Dis."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Zimenkov, D., and Ushtanit, A. (2025). Comparative Analysis of Evolutionary Distances Using the Genus Mycobacterium. Int. J. Mol. Sci., 26.","DOI":"10.3390\/ijms262110471"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Hoffman, P.S. (2020). Antibacterial Discovery: 21st Century Challenges. Antibiotics, 9.","DOI":"10.3390\/antibiotics9050213"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Belay, W.Y., Getachew, M., Tegegne, B.A., Teffera, Z.H., Dagne, A., Zeleke, T.K., Abebe, R.B., Gedif, A.A., Fenta, A., and Yirdaw, G. (2024). Mechanism of Antibacterial Resistance, Strategies and next-Generation Antimicrobials to Contain Antimicrobial Resistance: A Review. Front. Pharmacol., 15.","DOI":"10.3389\/fphar.2024.1444781"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1016\/j.coviro.2012.07.004","article-title":"Human Viral Diseases: What Is next for Antiviral Drug Discovery?","volume":"2","year":"2012","journal-title":"Curr. Opin. Virol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"14379","DOI":"10.1021\/acs.chemrev.6b00209","article-title":"Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs","volume":"116","author":"Shelton","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Alexandrova, L.A., Khandazhinskaya, A.L., Matyugina, E.S., Makarov, D.A., and Kochetkov, S.N. (2022). Analogues of Pyrimidine Nucleosides as Mycobacteria Growth Inhibitors. Microorganisms, 10.","DOI":"10.37247\/PAMICR3ED.3.22.7"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2156","DOI":"10.1093\/jac\/dkx151","article-title":"Repurposing of Nucleoside- and Nucleobase-Derivative Drugs as Antibiotics and Biofilm Inhibitors","volume":"72","author":"Yssel","year":"2017","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1038\/nrd4010","article-title":"Advances in the Development of Nucleoside and Nucleotide Analogues for Cancer and Viral Diseases","volume":"12","author":"Jordheim","year":"2013","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"855","DOI":"10.1038\/s41429-019-0237-1","article-title":"Discovery and Applications of Nucleoside Antibiotics beyond Polyoxin","volume":"72","author":"Osada","year":"2019","journal-title":"J. Antibiot."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1038\/s41429-019-0227-3","article-title":"Mechanism of Action of Nucleoside Antibacterial Natural Product Antibiotics","volume":"72","author":"Bugg","year":"2019","journal-title":"J. Antibiot."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"10343","DOI":"10.1021\/acs.jmedchem.6b00325","article-title":"Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?","volume":"59","author":"Serpi","year":"2016","journal-title":"J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"291","DOI":"10.4155\/fmc.14.166","article-title":"Nucleoside Analogs and Tuberculosis: New Weapons against an Old Enemy","volume":"7","author":"Ferrari","year":"2015","journal-title":"Future Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Platonova, Y.B., Volov, A.N., and Tomilova, L.G. (2020). The Synthesis and Antituberculosis Activity of 5-Alkynyl Uracil Derivatives. Bioorg. Med. Chem. Lett., 30.","DOI":"10.1016\/j.bmcl.2020.127351"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2083","DOI":"10.1134\/S1070428023120047","article-title":"Synthesis and Antitubercular Activity of New 5-Alkynyl Derivatives of 2-Thiouridine","volume":"59","author":"Platonova","year":"2023","journal-title":"Russ. J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"D303","DOI":"10.1093\/nar\/gkx1030","article-title":"MODOMICS: A Database of RNA Modification Pathways. 2017 Update","volume":"46","author":"Boccaletto","year":"2018","journal-title":"Nucleic Acids Res."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"9877","DOI":"10.1016\/S0040-4020(01)80190-3","article-title":"Sulfur- and Seleno-Sugar Modified Nucleosides. Synthesis, Chemical Transformations and Biological Properties","volume":"49","author":"Wnuk","year":"1993","journal-title":"Tetrahedron"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Scott, K.A., and Njardarson, J.T. (2019). Analysis of US FDA-Approved Drugs Containing Sulfur Atoms, Springer International Publishing.","DOI":"10.1007\/978-3-030-25598-5_1"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1080\/17460441.2022.2044783","article-title":"The Importance of Sulfur-Containing Motifs in Drug Design and Discovery","volume":"17","author":"Mustafa","year":"2022","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"486","DOI":"10.1016\/j.ejmech.2019.07.043","article-title":"Role of Sulphur-Heterocycles in Medicinal Chemistry: An Update","volume":"180","author":"Pathania","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"116732","DOI":"10.1016\/j.ejmech.2024.116732","article-title":"Thioamides in Medicinal Chemistry and as Small Molecule Therapeutic Agents","volume":"277","author":"Huang","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Maji, S., Debnath, B., Panda, S., Manna, T., Maity, A., Dayaramani, R., Nath, R., Khan, S.A., and Akhtar, M.J. (2024). Anticancer Potential of the S -Heterocyclic Ring Containing Drugs and Its Bioactivation to Reactive Metabolites. Chem. Biodivers., 21.","DOI":"10.1002\/cbdv.202400473"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2507","DOI":"10.1016\/S0960-894X(01)00471-1","article-title":"Bicyclic Anti-VZV Nucleosides: Thieno Analogues Retain Full Antiviral Activity","volume":"11","author":"Brancale","year":"2001","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"4088","DOI":"10.1016\/j.bmc.2012.05.004","article-title":"Discovery of Novel 5-(Ethyl or Hydroxymethyl) Analogs of 2\u2032-\u2018up\u2019 Fluoro (or Hydroxyl) Pyrimidine Nucleosides as a New Class of Mycobacterium Tuberculosis, Mycobacterium Bovis and Mycobacterium Avium Inhibitors","volume":"20","author":"Shakya","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4874","DOI":"10.1016\/j.bmc.2013.07.003","article-title":"Inhibition of Mycobacterium Tuberculosis Strains H37Rv and MDR MS-115 by a New Set of C5 Modified Pyrimidine Nucleosides","volume":"21","author":"Shmalenyuk","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"e202300366","DOI":"10.1002\/cmdc.202300366","article-title":"5-Substituted Uridines with Activity against Gram-Positive Bacteria","volume":"18","author":"Makarov","year":"2023","journal-title":"ChemMedChem"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Ostroumova, O.S., Efimova, S.S., Zlodeeva, P.D., Alexandrova, L.A., Makarov, D.A., Matyugina, E.S., Sokhraneva, V.A., Khandazhinskaya, A.L., and Kochetkov, S.N. (2024). Derivatives of Pyrimidine Nucleosides Affect Artificial Membranes Enriched with Mycobacterial Lipids. Pharmaceutics, 16.","DOI":"10.3390\/pharmaceutics16091110"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.biochi.2020.03.004","article-title":"Interaction of 5-Substituted Pyrimidine Nucleoside Analogues and M.tuberculosis: A View through an Electron Microscope","volume":"171\u2013172","author":"Khandazhinskaya","year":"2020","journal-title":"Biochimie"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"7131","DOI":"10.1016\/j.bmc.2015.09.053","article-title":"Synthesis and Evaluation of C-5 Modified 2\u2032-Deoxyuridine Monophosphates as Inhibitors of M. tuberculosis Thymidylate Synthase","volume":"23","author":"Alexandrova","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1038\/s41429-019-0273-x","article-title":"Synthesis of Water-Soluble Prodrugs of 5-Modified 2\u2032-Deoxyuridines and Their Antibacterial Activity","volume":"73","author":"Negrya","year":"2020","journal-title":"J. Antibiot."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1134\/S002689332101012X","article-title":"Glycol and Phosphate Depot Forms of 4- and\/or 5-Modified Nucleosides Exhibiting Antibacterial Activity","volume":"55","author":"Negrya","year":"2021","journal-title":"Mol. Biol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.mencom.2022.07.002","article-title":"Oligoglycol Carbonate Prodrugs of 5-Modified 2\u2032-Deoxyuridines: Synthesis and Antibacterial Activity","volume":"32","author":"Negrya","year":"2022","journal-title":"Mendeleev Communictions"},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Khatoon, H., and Abdulmalek, E. (2021). A Focused Review of Synthetic Applications of Lawesson\u2019s Reagent in Organic Synthesis. Molecules, 26.","DOI":"10.3390\/molecules26226937"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1039\/P19820001171","article-title":"4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-Triazol-1-yl)-1-(\u03b2-D-2,3,5-Tri-O-Acetylarabinofuranosyl)Pyrimidin-2(1H)-Ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(\u03b2-D-Arabinofuranosyl)Cytosine (Ara-C)","volume":"1","author":"Divakar","year":"1982","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1691","DOI":"10.1021\/jm00366a006","article-title":"Synthesis and Biological Activity of Various 3\u2032-Azido and 3\u2032-Amino Analogs of 5-Substituted Pyrimidine Deoxyribonucleosides","volume":"26","author":"Lin","year":"1983","journal-title":"J. Med. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2052","DOI":"10.1135\/cccc19652052","article-title":"Nucleic Acids Components and Their Analogues. LXI. The Reaction of Dimethylchloromethyleneammonium Chloride with the 2\u2032,3\u2032,5\u2032-Tri-O-Acyl Derivatives of Uridine and 6-Azauridine; A New Synthesis of 6-Azacytidine","volume":"30","year":"1965","journal-title":"Collect. Czechoslov. Chem. Commun."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1248\/cpb.36.945","article-title":"Alkyl Addition Reaction of Pyrimidine 2\u2032-Ketonucleosides: Synthesis of 2\u2032-Branched-Chain Sugar Pyrimidine Nucleosides. Nucleodides and Nucleotides. LXXXI","volume":"36","author":"Matsuda","year":"1988","journal-title":"Chem. Pharm. Bull."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/0022-1759(90)90309-J","article-title":"Towards an Optimized MTT Assay","volume":"130","author":"Otto","year":"1990","journal-title":"J. Immunol. Methods"},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Zimenkov, D. (2022). Variability of Mycobacterium Avium Complex Isolates Drug Susceptibility Testing by Broth Microdilution. Antibiotics, 11.","DOI":"10.3390\/antibiotics11121756"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1016\/j.jmb.2005.07.071","article-title":"Structure of the Mycobacterium Tuberculosis Flavin Dependent Thymidylate Synthase (MtbThyX) at 2.0\u00c5 Resolution","volume":"352","author":"Sampathkumar","year":"2005","journal-title":"J. Mol. Biol."},{"key":"ref_63","unstructured":"Chemical Computing Group Inc. (2012). Molecular Operating Environment (MOE), Chemical Computing Group Inc."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5210","DOI":"10.1021\/cr040650b","article-title":"Use of Lawesson\u2019s Reagent in Organic Syntheses","volume":"107","author":"Ozturk","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1055\/s-1988-27499","article-title":"Pyrimidine Derivatives; 1. The Highly Regioselective 4-Thionation of Pyrimidine-2,4(1H,3H)-Dione Derivatives with Lawesson Reagent","volume":"1988","author":"Kaneko","year":"1988","journal-title":"Synthesis"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1016\/0040-4039(95)00032-8","article-title":"An Unequivocal Synthesis of the Ring-A,B Dihydropyrromethenone of Phytochrome","volume":"36","author":"Jacobi","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1080\/104265090970197","article-title":"Synthesis of New Heterocyclic Compounds Using Lawesson Reagent","volume":"181","year":"2006","journal-title":"Phosphorus. Sulfur. Silicon Relat. Elem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"4207","DOI":"10.1021\/cr9001462","article-title":"Cu (I)-catalyzed Huisgen azide\u2212 alkyne 1, 3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry","volume":"109","author":"Amblard","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1128","DOI":"10.1016\/S1359-6446(03)02933-7","article-title":"The growing impact of click chemistry on drug discovery","volume":"8","author":"Kolb","year":"2003","journal-title":"Drug Discov. Today"},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Zimenkov, D., Zhuravlev, V., Ushtanit, A., Filippova, M., Semenova, U., Solovieva, N., Sviridenko, M., Khakhalina, A., Safonova, S., and Makarova, M. (2024). Biochip-Based Identification of Mycobacterial Species in Russia. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms252313200"},{"key":"ref_71","unstructured":"CLSI (2018). Susceptibility Testing of Mycobacteria, Nocardia Spp., and Other Aerobic Actinomycetes, CLSI. [3rd ed.]."},{"key":"ref_72","doi-asserted-by":"crossref","unstructured":"Parish, T., and Kumar, A. (2021). Methods in Molecular Biology. Mycobacteria Protocols, Springer.","DOI":"10.1007\/978-1-0716-1460-0"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1093\/protein\/8.2.127","article-title":"LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions","volume":"8","author":"Wallace","year":"1995","journal-title":"Protein Eng."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/23\/11712\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T15:04:05Z","timestamp":1764774245000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/23\/11712"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,3]]},"references-count":73,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2025,12]]}},"alternative-id":["ijms262311712"],"URL":"https:\/\/doi.org\/10.3390\/ijms262311712","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,12,3]]}}}