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Synthesis and Biological Evaluation of Novel Pyrazoles and Pyrazolo[3,4‐ d ]pyrimidines Incorporating a Benzenesulfonamide Moiety
Author(s) -
Ashour Hayam M. A.,
Wahab Abeer E. Abdel
Publication year - 2009
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200800178
Subject(s) - ampicillin , antimicrobial , chemistry , moiety , broad spectrum , biological activity , in vitro , clotrimazole , stereochemistry , leukemia , combinatorial chemistry , antibiotics , microbiology and biotechnology , biochemistry , antifungal , biology , organic chemistry , immunology
Synthesis and biological evaluation of novel pyrazoles and pyrazolo[3,4‐ d ]pyrimidines are reported. Fourteen compounds were selected by the NCI and tested for their preliminary in‐vitro anticancer activity, whereas all the synthesized compounds were evaluated for their in‐vitro antimicrobial activity. Compound 12a was proven to possess the highest anticancer activity with a broad spectrum profile. It showed particular effectiveness towards leukemia HL‐60 (TB), K‐562, non‐small cell lung cancer NCI‐H23, and colon cancer HT 29, KM 12 cell lines (GI 50 = 6.59, 4.44, 1.37, 3.33, and 9.63 μM, respectively). Out of the synthesized compounds, thirteen derivatives were found to display pronounced antimicrobial activity especially against P. aeruginosa. Compounds 2c , 5b , 10 , 11b , 17b , 18b , and 19 were proven to be the most active with a broad spectrum of activity. Compound 19 was found to be equipotent to ampicillin against B. subtilis , whereas compounds 11b and 19 were four times superior to ampicillin against P. aeruginosa , while compounds 5b and 18b were equipotent to ampicillin against the same organism. Moreover, compounds 2c , 10 , and 11b were nearly equipotent to ampicillin against E. coli . On the other hand, compounds 2c , 5b , 10 , 11a , 17b , and 18b exerted nearly half the activity of clotrimazole against C. albicans .