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Sci. Pharm. 2013, 81(2), 339-358; doi:10.3797/scipharm.1211-07

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

1
Department of Organometallic and Organometalloid Chemistry, National Research Centre, El-Behoos Street, Dokki, 12622 Cairo, Egypt
2
Department of Chemistry Natural and Microbial products, National Research Centre, El-Behoos Street, Dokki, 12622 Cairo, Egypt
3
Chemistry Department, Faculty of Science, Benha University, Benha, Egypt
4
Univet Pharmaceuticals Ltd, Balteem, Egypt
5
Biochemistry and Molecular Biology Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt
*
Author to whom correspondence should be addressed.
Received: 8 November 2012 / Accepted: 3 January 2013 / Published: 3 January 2013
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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; Pyrazolo[1,5-a]pyrimidines; Schiff bases; Antitumor agents; Ferrocenecarboxaldehyde 5-Aminopyrazole-4-carboxamides; Pyrazolo[1,5-a]pyrimidines; Schiff bases; Antitumor agents; Ferrocenecarboxaldehyde
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

HAFEZ, T.S.; OSMAN, S.A.; YOSEF, H.A.A.; EL-ALL, A.S.A.; HASSAN, A.S.; EL-SAWY, A.A.; ABDALLAH, M.M.; YOUNS, M. Synthesis, Structural Elucidation, and In Vitro Antitumor Activities of Some Pyrazolopyrimidines and Schiff Bases Derived from 5-Amino-3-(arylamino)-1H-pyrazole-4-carboxamides. Sci. Pharm. 2013, 81, 339-358.

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