1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds
oleh: 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
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2022-11-01 |
Deskripsi
A series of 11-substituted 3,5,10,11-tetrahydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>][1,3]thiazole-2,5,10-triones were obtained via <i>hetero</i>-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 <b>3.5</b> and <b>3.6</b> were screened for their anticancer activity; 11-Phenethyl-3,11-dihydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>]thiazole-2,5,10-trione (<b>3.6</b>) 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 <b>3.6</b> on p53-deficient colon carcinoma cells was two times weaker than on HCT116wt, and it may be an interesting feature of the mechanism action.