Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives

Ashraf S Hassan; Taghrid S Hafez; Souad A Osman

doi:10.3797/scipharm.1409-14

Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives

Sci Pharm. 2014 Oct 24;83(1):27-39. doi: 10.3797/scipharm.1409-14. Print 2015 Jan-Mar.

Authors

Ashraf S Hassan¹, Taghrid S Hafez¹, Souad A Osman¹

Affiliation

¹ Department of Organometallic and Organometalloid Chemistry, National Research Centre, El-Buhoth St, Cairo, Doki, Egypt.

Abstract

5-Amino-N-aryl-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamides 4a-c were synthesized by the reaction of N-(aryl)-2-cyano-3-[(4-methoxyphenyl)amino]-3-(methylthio)acrylamides 3a-c with hydrazine hydrate in ethanol. The reaction of 5-amino-N-aryl-1H-pyrazoles 4a-c with acetylacetone 5 or 2-(4-methoxybenzylidene)malononitrile 8 yielded the pyrazolo[1,5-a]pyrimidine derivatives 7a-c and 10a-c, respectively. The structures of the synthesized compounds were established based on elemental analysis and spectral data (IR, MS, (1)H-NMR, and (13)C-NMR). Representative examples of the new synthesized products were screened for their in vitro cytotoxic activity against Ehrlich Ascites Carcinoma (EAC) cells.

Keywords: 5-Aminopyrazoles; Cytotoxic activity; Ketene N,S-acetals; N-Substituted cyanoacetamide; Pyrazolo[1,5-a]pyrimidines.