{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T23:02:23Z","timestamp":1790118143322,"version":"4.0.1"},"reference-count":34,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T00:00:00Z","timestamp":1719187200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Innovative Development Agency of RUz","award":["F-FA-2021-360"],"award-info":[{"award-number":["F-FA-2021-360"]}]},{"name":"Innovative Development Agency of RUz","award":["24-14-00458"],"award-info":[{"award-number":["24-14-00458"]}]},{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["F-FA-2021-360"],"award-info":[{"award-number":["F-FA-2021-360"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["24-14-00458"],"award-info":[{"award-number":["24-14-00458"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>1,2,4-Triazole derivatives have a wide range of biological activities. The most well-known drug that contains 1,2,4-triazole as part of its structure is the nucleoside analogue ribavirin, an antiviral drug. Finding new nucleosides based on 1,2,4-triazole is a topical task. The aim of this study was to synthesize ribosides and deoxyribosides of 1,2,4-triazole-3-thione derivatives and test their antiviral activity against herpes simplex viruses. Three compounds from a series of synthesized mono- and disubstituted 1,2,4-triazole-3-thione derivatives were found to be substrates for E. coli purine nucleoside phosphorylase. Of six prepared nucleosides, the riboside and deoxyriboside of 3-phenacylthio-1,2,4-triazole were obtained at good yields. The yields of the disubstituted 1,2,4-triazol-3-thiones were low due to the effect of bulky substituents at the C3 and C5 positions on the selectivity of enzymatic glycosylation for one particular nitrogen atom in the triazole ring. The results of cytotoxic and antiviral studies on acyclovir-sensitive wild-type strain HSV-1\/L2(TK+) and acyclovir-resistant strain (HSV-1\/L2\/RACV) in Vero E6 cell culture showed that the incorporation of a thiobutyl substituent into the C5 position of 3-phenyl-1,2,4-triazole results in a significant increase in the cytotoxicity of the base and antiviral activity. The highest antiviral activity was observed in the 3-phenacylthio-1-(\u03b2-D-ribofuranosyl)-1,2,4-triazole and 5-butylthio-1-(2-deoxy-\u03b2-D-ribofuranosyl)-3-phenyl-1,2,4-triazole nucleosides, with their selectivity indexes being significantly higher than that of ribavirin. It was also found that with the increasing lipophilicity of the nucleosides, the activity and toxicity of the tested compounds increased.<\/jats:p>","DOI":"10.3390\/biom14070745","type":"journal-article","created":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T10:41:12Z","timestamp":1719225672000},"page":"745","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis of Substituted 1,2,4-Triazole-3-Thione Nucleosides Using E. coli Purine Nucleoside Phosphorylase"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8571-4197","authenticated-orcid":false,"given":"Ilya V.","family":"Fateev","sequence":"first","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1863-7117","authenticated-orcid":false,"given":"Sobirdjan A.","family":"Sasmakov","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaloliddin M.","family":"Abdurakhmanov","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdukhakim A.","family":"Ziyaev","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4773-7117","authenticated-orcid":false,"given":"Shukhrat Sh.","family":"Khasanov","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3054-6111","authenticated-orcid":false,"given":"Farkhod B.","family":"Eshboev","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oybek N.","family":"Ashirov","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valeriya D.","family":"Frolova","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9552-7141","authenticated-orcid":false,"given":"Barbara Z.","family":"Eletskaya","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Olga S.","family":"Smirnova","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5684-8188","authenticated-orcid":false,"given":"Maria Ya.","family":"Berzina","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra O.","family":"Arnautova","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9904-1539","authenticated-orcid":false,"given":"Yulia A.","family":"Abramchik","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria A.","family":"Kostromina","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3413-0180","authenticated-orcid":false,"given":"Alexey L.","family":"Kayushin","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantin V.","family":"Antonov","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander S.","family":"Paramonov","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valeria L.","family":"Andronova","sequence":"additional","affiliation":[{"name":"D. I. Ivanovsky Institute of Virology (N. F. Gamaleya Research Center of Epidemiology and Microbiology, Ministry of Healthcare of the Russian Federation), Gamaleya St. 18, 123098 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Georgiy A.","family":"Galegov","sequence":"additional","affiliation":[{"name":"D. I. Ivanovsky Institute of Virology (N. F. Gamaleya Research Center of Epidemiology and Microbiology, Ministry of Healthcare of the Russian Federation), Gamaleya St. 18, 123098 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3231-5838","authenticated-orcid":false,"given":"Roman S.","family":"Esipov","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shakhnoz S.","family":"Azimova","sequence":"additional","affiliation":[{"name":"Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anatoly I.","family":"Miroshnikov","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina D.","family":"Konstantinova","sequence":"additional","affiliation":[{"name":"Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16\/10, 117997 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1126\/science.177.4050.705","article-title":"Broad-spectrum antiviral activity of virazole: 1-\u03b2-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide","volume":"177","author":"Sidwell","year":"1972","journal-title":"Science"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1016\/j.eimc.2018.05.008","article-title":"Use of ribavirin in viruses other than hepatitis C. 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