{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T20:29:30Z","timestamp":1791318570904,"version":"4.3.1"},"reference-count":235,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T00:00:00Z","timestamp":1759881600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100019648","name":"Kuban Science Foundation","doi-asserted-by":"crossref","award":["N-24.1\/30"],"award-info":[{"award-number":["N-24.1\/30"]}],"id":[{"id":"10.13039\/100019648","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The aim of this work was to prepare new heterodimeric molecules containing pharmacophoric fragments of 3-cyanoquinoline\/3-aminothieno[2,3-b]pyridine\/3-aminothieno[2,3-b]quinoline on one side and phenothiazine on the other. The products were synthesized via selective S-alkylation of readily available 2-thioxo-3-cyanopyridines or -quinolines with N-(chloroacetyl)phenothiazines, followed by base-promoted Thorpe\u2013Ziegler isomerization of the resulting N-[(3-cyanopyridin-2-ylthio)acetyl]phenothiazines. We found that both the S-alkylation and the Thorpe\u2013Ziegler cyclization reactions, when conducted with KOH under heating, were accompanied to a significant extent by a side reaction involving the elimination of phenothiazine. Optimization of the conditions (0\u20135 \u00b0C, anhydrous N,N-dimethylacetamide and NaH or t-BuONa as non-nucleophilic bases) minimized the side reaction and increased the yields of the target heterodimers. The structures of the products were confirmed by IR spectroscopy, 1H, and 13C DEPTQ NMR studies. It was demonstrated that the synthesized 3-aminothieno[2,3-b]pyridines can be acylated with chloroacetyl chloride in hot chloroform. The resulting chloroacetamide derivative reacts with potassium thiocyanate in DMF to form the corresponding 2-iminothiazolidin-4-one; in this process, phenothiazine elimination does not occur, and the Gruner\u2013Gewald rearrangement product was not observed. The structural features and spectral characteristics of the synthesized 2-iminothiazolidin-4-one derivative were investigated by quantum chemical methods at the B3LYP-D4\/def2-TZVP level. A range of drug-relevant properties was also evaluated using in silico methods, and ADMET parameters were calculated. A molecular docking study identified a number of potential protein targets for the new heterodimers, indicating the promise of these compounds for the development of novel antitumor agents.<\/jats:p>","DOI":"10.3390\/ijms26199798","type":"journal-article","created":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T14:06:53Z","timestamp":1759932413000},"page":"9798","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis of New Phenothiazine\/3-cyanoquinoline and Phenothiazine\/3-aminothieno[2,3-b]pyridine(-quinoline) Heterodimers"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7163-0497","authenticated-orcid":false,"given":"Victor V.","family":"Dotsenko","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"},{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-9960-9440","authenticated-orcid":false,"given":"Vladislav K.","family":"Kindop","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9005-9668","authenticated-orcid":false,"given":"Vyacheslav K.","family":"Kindop","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eva S.","family":"Daus","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3435-4873","authenticated-orcid":false,"given":"Igor V.","family":"Yudaev","sequence":"additional","affiliation":[{"name":"Faculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9120-7637","authenticated-orcid":false,"given":"Yuliia V.","family":"Daus","sequence":"additional","affiliation":[{"name":"Faculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander V.","family":"Bespalov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9812-0144","authenticated-orcid":false,"given":"Dmitrii S.","family":"Buryi","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7685-1448","authenticated-orcid":false,"given":"Darya Yu.","family":"Lukina","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7125-9066","authenticated-orcid":false,"given":"Nicolai A.","family":"Aksenov","sequence":"additional","affiliation":[{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Inna V.","family":"Aksenova","sequence":"additional","affiliation":[{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,10,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"113768","DOI":"10.1016\/j.ejmech.2021.113768","article-title":"Molecular hybrids: A five-year survey on structures of multiple targeted hybrids of protein kinase inhibitors for cancer therapy","volume":"225","author":"Soltan","year":"2021","journal-title":"Eur. 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