Y. Matiichuk, Y. Horak, T. Chaban
Oct 1, 2020
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Journal
Russian Journal of Organic Chemistry
Abstract
Reactions of 5-(1,3-benzothiazol-2-yl)furan-2-carbaldehyde with 2-acetylfuran, 2-acetylthiophene, and some compounds containing an active methylene group gave a number of new 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-1-(furan- or thiophen-2-yl)prop-2-en-1-one, 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]acrylonitrile, 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-2-cyanoacrylamide, and 5-{[5-(1,3-benzothiazol-2-yl)furan-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one derivatives. 5-{[5-(1,3-Benzothiazol-2-yl)furan-2-yl]methylidene}-2-(morpholin-4-yl)-1,3-thiazol-4-one and diethyl 4-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate were synthesized by multicomponent reactions involving the title compound. Antitumor screening of the synthesized 5-(1,3-benzothiazol-2-yl)furan-2-carbaldehyde derivatives revealed a lead compound, 3-[5-(1,3-benzothiazol-2-yl)furan-2-yl]-2-(4-phenyl-1,3-thiazol-2-yl)prop-2-enenitrile, which proved to be superior to 5-fluorouracil, cisplatin, and curcumin taken as reference drugs.