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5-(1,3-Benzothiazol-2-yl)furan-2-carbaldehyde in the Design of Antitumor Agents

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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.

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Authors and Affiliations

  1. Danilo Halytsky Lviv National Medical University, 79010, Lviv, Ukraine

    Yu. E. Matiichuk, T. I. Chaban & V. Ya. Horishny

  2. Ivan Franko Lviv National University, 79005, Lviv, Ukraine

    Y. I. Horak, O. S. Tymoshuk & V. S. Matiychuk

Authors
  1. Yu. E. Matiichuk
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  2. Y. I. Horak
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  3. T. I. Chaban
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  4. V. Ya. Horishny
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  5. O. S. Tymoshuk
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  6. V. S. Matiychuk
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Correspondence to V. S. Matiychuk.

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Matiichuk, Y.E., Horak, Y.I., Chaban, T.I. et al. 5-(1,3-Benzothiazol-2-yl)furan-2-carbaldehyde in the Design of Antitumor Agents. Russ J Org Chem 56, 1720–1727 (2020). https://doi.org/10.1134/S1070428020100085

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