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

Molecules. 2022 Nov 4;27(21):7575. doi: 10.3390/molecules27217575.


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.

Keywords: 1,4-naphthoquinones; DNA intercalation; X-ray; anticancer activity; cytotoxicity; hetero-Diels-Alder reaction; thiopyrano[2,3-d]thiazoles.

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Drug Screening Assays, Antitumor
  • Naphthoquinones* / chemistry
  • Thiazoles / chemistry
  • Tumor Suppressor Protein p53


  • 1,4-naphthoquinone
  • Thiazoles
  • Tumor Suppressor Protein p53
  • Naphthoquinones
  • Antineoplastic Agents