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Abstract

DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL PYRAZOLE, PYRIMIDINE AND THIAZOLE DERIVATIVES ATTACHED TO NAPHTHALENE MOIETY AS ANTICANCER AND ANTIMICROBIAL AGENTS

Zakaria K. Abdel –Samii*, Hanan A. Abdel- Fattah* and Reham M. Abdel- Rehem.

ABSTRACT

New N-thiocarbamoyl pyrazole derivatives 2a-d and 3,4-dihydro pyrimidine-2(1H)-thione derivatives 3a-d were synthesized from the reaction of α,β-unsaturated ketones 1a-d with thiosemicarbazide and thiourea respectively. N-thiocarbamoyl pyrazole derivatives 2a-d used as key intermediate for synthesis of some new pyrazolothiazoles 4-19 and pyrazolothiazol-4(5H)-ones 20-22 via cyclization using either phenacyl bromide derivatives or ethyl bromo acetate respectively. The newly synthesized compounds were elucidated by IR, 1HNMR, Mass spectrometry and Micro analysis. Some of the new compounds were evaluated for their anticancer activity against breast carcinoma (MCF- 7) and colon carcinoma (HCT-116) cell lines. The anticancer activity showed that the tested compounds have promising antitumor activity against the two cell lines. Compounds 3d, 6,12,13,19,22 showed high activity against the two cell lines. Compound 13 was the most active one against the two cell lines with IC50 (1.01, 1.22ug/ml). Molecular docking studies were performed in order to rationalize the obtained biological results. On the other hand, the antimicrobial activity evaluation of some new compounds showed that most of the tested compounds exhibited promising antibacterial as well as antifungal activities.

Keywords: Docking, Synthesis, Pyrazole, Pyrimidine, Thiazole derivatives, Anticancer, Antimicrobial activities.


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