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Sci Pharm. 2013 Apr-Jun;81(2):339-57. doi: 10.3797/scipharm.1211-07. Epub 2013 Jan 3.

Synthesis, Structural Elucidation, and In Vitro Antitumor Activities of Some Pyrazolopyrimidines and Schiff Bases Derived from 5-Amino-3-(arylamino)-1H-pyrazole-4-carboxamides.

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1
Department of Organometallic and Organometalloid Chemistry, National Research Centre, El-Behoos Street, Dokki, 12622 Cairo, Egypt.

Abstract

The reaction of 5-amino-3-(arylamino)-1H-pyrazole-4-carboxamides 1a,b with acetylacetone 2 and arylidenemalononitriles 5a-c yielded the pyrazolo[1,5-a]-pyrimidine derivatives 4a,b and 7a-f respectively. On the other hand, Schiff bases 9a,b and 12a-j were obtained upon treatment of carboxamides 1a,b with isatin 8 and some selected aldehydes 11a-e. The newly synthesized compounds were characterized by analytical and spectroscopic data. Representative examples of the synthesized products 4a,b, 7e, 7f, 9b, 12b-f, 12h, and 12j were screened for their in vitro antitumor activities against different human cancer cell lines and the structure-activity relationship (SAR) was discussed.

KEYWORDS:

5-Aminopyrazole-4-carboxamides; Antitumor agents; Ferrocenecarboxaldehyde; Pyrazolo[1,5-a]pyrimidines; Schiff bases

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