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

Bioorg Med Chem Lett. 2010 May 15;20(10):3169-72. doi: 10.1016/j.bmcl.2010.03.083. Epub 2010 Mar 29.

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 microg/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 microM 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 2mg/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.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology
  • Staphylococcus aureus / drug effects

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Anti-Infective Agents
  • Pyrazoles