Novel 1,3,5-triphenyl-2pyrazolines as anti-infective agents.

Sivakumar, P.M.; Seenivasan, S.P.; Kumar, V.; Double, M.

Bioorganic & Medicinal Chemistry Letters; 2010; 20; 3169-3172.             

Abstract: Sixteen 1,3,5-triphenyl-2-pyrazolines were synthesized and their anti-infective activities (against Mycobacterium tuberculosis H 37 Rv, six bacterial and four fungal strains) were tested. Only compound with SO 2 CH 3 in the para position of the A-ring was active against the tubercular strain at 100 m g/ml concentration. All compounds showed good anti infective activity against Escherichia coli and poor activity against Staphylococcus aureus. Compounds 4, 12, 13 and 14 exhibited reasonable activity against all the organisms tested (<0.309 m M except against S. aureus . The activity of these compounds correlated with their lipophilic/hydrophilic nature. Compounds 4, 10 and 16 showed very good activity (>88% reduction) against four fungi studied at 2 mg/ml. All these compounds possess halogen substitutions. Compound 11 showed very high activity (>90%) against three fungi. Majority of the compounds showed more than 90% inhibition against one or two fungi. Since pyrazolines are reported to inhibit the activity of p-glycoprotein, they may prevent drug resistance developed by microorganism.

Keywords: 1,3,5-Triphenyl-2-pyrazolines; A log P ; Mycobacterium tuberculosis H 37 Rv; High resolution mass spectrum (HR-MS)

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