| Summary: | 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.
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