1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-d]thiazoles as Potential Biologically Active Compounds
Lozynskyi A. Senkiv J. Ivasechko I. Finiuk N. Klyuchivska O. Kashchak N. Lesyk D. Karkhut A. Polovkovych S. Levytska O. Karpenko O. Boshkayeva A. Sayakova G. Gzella A. Stoika R. Lesyk R.
November 2022MDPI
Molecules
2022#27Issue 21
A series of 11-substituted 3,5,10,11-tetrahydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]thiazole-2,5,10-triones were obtained via hetero-Diels-Alder reaction of 5-alkyl/arylallylidene/-4-thioxo-2-thiazolidinones and 1,4-naphthoquinones. The structures of newly synthesized compounds were established by spectral data and a single-crystal X-ray diffraction analysis. According to U.S. NCI protocols, compounds 3.5 and 3.6 were screened for their anticancer activity; 11-Phenethyl-3,11-dihydro-2H-benzo[6,7]thiochromeno[2,3-d]thiazole-2,5,10-trione (3.6) showed pronounced cytotoxic effect on leukemia (Jurkat, THP-1), epidermoid (KB3-1, KBC-1), and colon (HCT116wt, HCT116 p53-/-) cell lines. The cytotoxic action of 3.6 on p53-deficient colon carcinoma cells was two times weaker than on HCT116wt, and it may be an interesting feature of the mechanism action.
1,4-naphthoquinones , anticancer activity , cytotoxicity , DNA intercalation , hetero-Diels-Alder reaction , thiopyrano[2,3-d]thiazoles , X-ray
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Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv, 79010, Ukraine
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, Lviv, 79005, Ukraine
Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, Lviv, 79013, Ukraine
Department of Organization and Economics of Pharmacy, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv, 79010, Ukraine
Enamine Ltd., 23 Alexandra Matrosova, Kyiv, 01103, Ukraine
Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty, 050000, Kazakhstan
Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, Poznan, 60-780, Poland
Department of Biotechnology and Cell Biology, Medical College, University of Information Technology and Management in Rzeszow, Sucharskiego 2, Rzeszow, 35-225, Poland
Department of Pharmaceutical
Institute of Cell Biology of National Academy of Sciences of Ukraine
Department of Technology of Biologically Active Substances
Department of Organization and Economics of Pharmacy
Enamine Ltd.
Department of Pharmaceutical and Toxicological Chemistry
Department of Organic Chemistry
Department of Biotechnology and Cell Biology
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