1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds
Andrii Lozynskyi,
Julia Senkiv,
Iryna Ivasechko,
Nataliya Finiuk,
Olga Klyuchivska,
Nataliya Kashchak,
Danylo Lesyk,
Andriy Karkhut,
Svyatoslav Polovkovych,
Oksana Levytska,
Olexandr Karpenko,
Assyl Boshkayeva,
Galiya Sayakova,
Andrzej Gzella,
Rostyslav Stoika,
Roman Lesyk
Affiliations
Andrii Lozynskyi
Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
Julia Senkiv
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Iryna Ivasechko
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Nataliya Finiuk
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Olga Klyuchivska
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Nataliya Kashchak
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Danylo Lesyk
Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
Andriy Karkhut
Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, Ukraine
Svyatoslav Polovkovych
Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandera 12, 79013 Lviv, Ukraine
Oksana Levytska
Department of Organization and Economics of Pharmacy, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
Olexandr Karpenko
Enamine Ltd., 23 Alexandra Matrosova, 01103 Kyiv, Ukraine
Assyl Boshkayeva
Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan
Galiya Sayakova
Department of Pharmaceutical and Toxicological Chemistry, Pharmacognosy and Botany, Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan
Andrzej Gzella
Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
Rostyslav Stoika
Institute of Cell Biology of National Academy of Sciences of Ukraine, Drahomanov14/16, 79005 Lviv, Ukraine
Roman Lesyk
Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, 79010 Lviv, Ukraine
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.
