1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3- d ]thiazoles as Potential Biologically Active Compounds.

Autor: Lozynskyi A; Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine., Senkiv J; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Ivasechko I; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Finiuk N; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Klyuchivska O; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Kashchak N; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Lesyk D; Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine., Karkhut A; Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, Ukraine., Polovkovych S; Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, Ukraine., Levytska O; Department of Organization and Economics of Pharmacy, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine., Karpenko O; Enamine Ltd., 23 Alexandra Matrosova, 01103 Kyiv, Ukraine., Boshkayeva A; Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan., Sayakova G; Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan., Gzella A; Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland., Stoika R; Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine., Lesyk R; Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine.; Department of Biotechnology and Cell Biology, Medical College, University of Information Technology and Management in Rzeszow, Sucharskiego 2, 35-225 Rzeszow, Poland.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2022 Nov 04; Vol. 27 (21). Date of Electronic Publication: 2022 Nov 04.
DOI: 10.3390/molecules27217575
Abstrakt: A series of 11-substituted 3,5,10,11-tetrahydro-2 H -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-2 H -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.
Databáze: MEDLINE
Nepřihlášeným uživatelům se plný text nezobrazuje