{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T10:41:52Z","timestamp":1785840112488,"version":"3.56.0"},"reference-count":39,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2024,10,11]],"date-time":"2024-10-11T00:00:00Z","timestamp":1728604800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian science foundation (RSF)","doi-asserted-by":"publisher","award":["23-25-00382"],"award-info":[{"award-number":["23-25-00382"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Ribavirin and its analogues exhibit an in vitro antiproliferative effect in cancer cells. In this work, we studied the biological activities of a number of alkyl\/aryloxymethyl derivatives of ribavirin\u2019s aglycon\u20141,2,4-triazole-3-carboxamide. Alkyl\/arylxymethyl derivatives of 1,2,4-triazole-3-carboxamide with substitutions at the fifth or first position of the triazole ring, were synthesized and their antiproliferative and antimicrobial effects were assessed. For both series, the presence of an antiproliferative effect was investigated, and 1-alkyl\/aryloxymethyl derivatives were shown an antimicrobial potential against a Gram-positive bacteria Micrococcus luteus and Gram-negative bacterium Pseudomonas aeruginosa. The obtained results showed that the n-decyloxymethyl derivatives induced leukemia cell death at low micromolar concentrations. We confirmed that n-decyloxymethyl derivatives of ribavirin inhibited the cell cycle progression and induced an accumulation of leukemia cells in the subG1-phase. The molecular docking results suggest that alkyl\/aryloxymethyl derivatives may act by inhibiting translation initiation, due to interference with eIF4E assembly. The outcome results revealed that active derivatives (1- or 5-n-decyloxymethyl-1,2,4-triazole-3-carboxamides) can be considered as a lead compound for anticancer treatments.<\/jats:p>","DOI":"10.3390\/molecules29204808","type":"journal-article","created":{"date-parts":[[2024,10,11]],"date-time":"2024-10-11T08:10:16Z","timestamp":1728634216000},"page":"4808","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of Alkyl\/Aryloxymethyl Derivatives of 1,2,4-Triazole-3-Carboxamides and Their Biological Activities"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0006-2511-3628","authenticated-orcid":false,"given":"Ekaterina A.","family":"Mikhina","sequence":"first","affiliation":[{"name":"Lomonosov Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadsky Prospekt, Moscow 119571, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-0056-6040","authenticated-orcid":false,"given":"Daria V.","family":"Stepanycheva","sequence":"additional","affiliation":[{"name":"Department of Chemical Carcinogenesis, N.N. Blokhin Russian Cancer Research Center, Ministry of Health of Russia, 24 Kashirskoe Shosse, Moscow 115478, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0896-2952","authenticated-orcid":false,"given":"Varvara P.","family":"Maksimova","sequence":"additional","affiliation":[{"name":"Department of Chemical Carcinogenesis, N.N. Blokhin Russian Cancer Research Center, Ministry of Health of Russia, 24 Kashirskoe Shosse, Moscow 115478, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0063-4922","authenticated-orcid":false,"given":"Olga N.","family":"Sineva","sequence":"additional","affiliation":[{"name":"Gause Institute of New Antibiotics, 11 Bolshaya Pirogovskaya St., Moscow 119021, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0759-721X","authenticated-orcid":false,"given":"Natalia N.","family":"Markelova","sequence":"additional","affiliation":[{"name":"Gause Institute of New Antibiotics, 11 Bolshaya Pirogovskaya St., Moscow 119021, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lyubov E.","family":"Grebenkina","sequence":"additional","affiliation":[{"name":"Lomonosov Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadsky Prospekt, Moscow 119571, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1967-9637","authenticated-orcid":false,"given":"Ekaterina A.","family":"Lesovaya","sequence":"additional","affiliation":[{"name":"Department of Chemical Carcinogenesis, N.N. Blokhin Russian Cancer Research Center, Ministry of Health of Russia, 24 Kashirskoe Shosse, Moscow 115478, Russia"},{"name":"Faculty of Oncology, I.P. Pavlov Ryazan State Medical University, Ministry of Health of Russia, 9 Vysokovol\u2019tnaya St., Ryazan 390026, Russia"},{"name":"Laboratory of Single Cell Biology, Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9710-8178","authenticated-orcid":false,"given":"Marianna G.","family":"Yakubovskaya","sequence":"additional","affiliation":[{"name":"Department of Chemical Carcinogenesis, N.N. Blokhin Russian Cancer Research Center, Ministry of Health of Russia, 24 Kashirskoe Shosse, Moscow 115478, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0830-3036","authenticated-orcid":false,"given":"Andrey V.","family":"Matveev","sequence":"additional","affiliation":[{"name":"Lomonosov Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadsky Prospekt, Moscow 119571, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3318-9391","authenticated-orcid":false,"given":"Ekaterina M.","family":"Zhidkova","sequence":"additional","affiliation":[{"name":"Department of Chemical Carcinogenesis, N.N. Blokhin Russian Cancer Research Center, Ministry of Health of Russia, 24 Kashirskoe Shosse, Moscow 115478, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,10,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"7","DOI":"10.32362\/2410-6593-2019-14-4-7-23","article-title":"Ribavirin and its analogues: Can you teach an old dog new tricks?","volume":"14","author":"Chudinov","year":"2019","journal-title":"Fine Chem. Technol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"116850","DOI":"10.1016\/j.bmc.2022.116858","article-title":"Anti-HCV and Zika activities of ribavirin C-nucleosides analogues","volume":"68","author":"Gonzalez","year":"2022","journal-title":"Bioorg. Med. Chem."},{"key":"ref_3","first-page":"2050","article-title":"Colloid-Chemical and Antimicrobial Properties of Ribavirin Aqueous Solutions","volume":"11","author":"Sardushkin","year":"2020","journal-title":"Sys. 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