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

Abstract

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.

Thiazole as an Indispensable Scaffold in Anti‐Leukemic Agents: A Semicentennial Review

“…The acute monocytic leukemia patient‘s THP‐1 cells, which were isolated monocytes from peripheral blood, also responded favorably to treatment with 183 . This substance‘s IC 50 was 7.94 μM [48] …”

“…This substance's IC 50 was 7.94 μM. [48] A different type of thiazole derivatives showed good activity against leukemia cell lines.…”

Update on thiopyran-fused heterocycle synthesis (2013–2024)

“…Detailed anticancer screening was also reported for the adducts obtained by the reaction of the Knoevenagel adduct (of isorhodanine with aliphatic aldehydes) with 1,4naphthoquinone. 79 Scheme 47 Synthesis of thiopyrano [2,3-d]thiazoles from 4-thioxo-2-thiazolidinone incorporating an arylsulfonate moiety.…”

“…Detailed anticancer screening was also reported for the adducts obtained by the reaction of the Knoevenagel adduct (of isorhodanine with aliphatic aldehydes) with 1,4-naphthoquinone. 79…”