Multi-component synthesis of pyrazolo[1,5-a]quinazoline, thiazole and thiophene derivatives as cytotoxic agents

Abstract

ABSTRACT. This study demonstrated the synthesis of a number of pyrazolo[1,5-a]quinazoline derivatives about 24 products based on the starting material 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 1a-f. Moreover, other ring systems including thiophene, pyrazole, thiazole and pyran (16 compounds) were prepared based on another starting compounds 2-(furan-2-ylmethylene)cyclohexane-1,3-dione 10 and 5,5-dimethyl-3-phenyl-2-thioxo-2,3,5,6-tetrahydrobenzo[d]thiazol-7(4H)-one 18. The multi-component reaction was used to prepare all the previous compounds. The structures of all the synthesised compounds were confirmed by the analytical and spectral data. Some selected compounds were chosen to test their anticancer activity against six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, SMMC-7721 and, H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. Toward the tested cell lines, nine compounds were the most cytotoxic compounds. The results obtained revealed that the synthesized compounds are good cytotoxic agents and of great impact for future work.
 KEY WORDS: Multi-component reactions, Pyrazolo[1,5-a]quinazoline, Thiophene, Thiazole, Cytotoxicity
 Bull. Chem. Soc. Ethiop. 2023, 37(6), 1521-1538. DOI: https://dx.doi.org/10.4314/bcse.v37i6.17