{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T04:39:46Z","timestamp":1790311186418,"version":"4.1.0"},"reference-count":57,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2025,9,21]],"date-time":"2025-09-21T00:00:00Z","timestamp":1758412800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,9,21]],"date-time":"2025-09-21T00:00:00Z","timestamp":1758412800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2025,12,15]]},"abstract":"<jats:p>\n                    A novel chemotype of nitrile\u2010containing azolopyrimidines with potential antitumor activity has been proposed, and a method for the synthesis of the corresponding 5\u2010amino\u20107\u2010oxoazolo[1,5\u2010\n                    <jats:italic>a<\/jats:italic>\n                    ]pyrimidine\u20106\u2010carbonitriles by cyclocondensation of various aminoazoles and ethyl 2\u2010cyano\u20103\u2010R\u2010amino\u20103\u2010(methylsulfanyl)acrylates has been developed. Cytotoxic effects of the obtained azolopyrimidines against glioblastoma (A\u2010172), bladder carcinoma (T\u201024), lung carcinoma (A\u2010549), and human embryonic kidney (HEK\u2010293) cells have been investigated, and structure\u2013activity relationships have been identified. 2\u2010Phenyl\u20105\u2010(morpholin\u20104\u2010yl)\u20107\u2010oxo\u20101,2,4\u2010triazolo[1,5\u2010\n                    <jats:italic>a<\/jats:italic>\n                    ]pyrimidine\u20106\u2010carbonitrile\n                    <jats:bold>5j<\/jats:bold>\n                    has been found to exhibit selective cytotoxic activity against the T\u201024 cells (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u200914.68\u2009\u00b5M), whereas 3\u2010bromo\u20105\u2010(morpholin\u20104\u2010yl)\u20107\u2010oxopyrazolo[1,5\u2010\n                    <jats:italic>a<\/jats:italic>\n                    ]pyrimidine\u20106\u2010carbonitrile\n                    <jats:bold>5v<\/jats:bold>\n                    has shown selective toxicity against the A\u2010172 cells (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u200918.38\u2009\u00b5M). Further studies on heterocycle\n                    <jats:bold>5j<\/jats:bold>\n                    in the annexin V apoptosis assay indicate that the primary mechanism involves inhibition of proliferative activity rather than induction of cell death. The cyclin\u2010dependent kinase\u00a02 protein is suggested as a possible target for the cytotoxic action of the studied compounds\n                    <jats:bold>5<\/jats:bold>\n                    on the T\u201024 cell line according to the notable correlation between docking studies and MTT assay results.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.202500535","type":"journal-article","created":{"date-parts":[[2025,9,21]],"date-time":"2025-09-21T23:38:57Z","timestamp":1758497937000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["5\u2010Amino\u20107\u2010Oxo\u20104,7\u2010Dihydroazolo[1,5\u2010a]pyrimidine\u20106\u2010Carbonitriles: Synthesis and Study of Antitumor Effect In\u2009Vitro and In\u2009Silico"],"prefix":"10.1002","volume":"20","author":[{"given":"Veronika V.","family":"Dolgova","sequence":"first","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. 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Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ekaterina A.","family":"Lvova","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilya I.","family":"Butorin","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elena A.","family":"Fesenko","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vsevolod V.","family":"Melekhin","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"},{"name":"Department of Medical Biology and Genetics Ural State Medical University  Repina st. 3 Yekaterinburg 620028 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria D.","family":"Tokhtueva","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. Eltsin  Mira st. 19 Yekaterinburg 620002 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastasiya V.","family":"Paramonova","sequence":"additional","affiliation":[{"name":"Scientifc, Educational and Innovative Center of Chemical and Pharmaceutical Technologies Ural Federal University named after the First President of Russia B.N. 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