New nitric oxide donating 1,2,4-triazole/oxime hybrids: synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities

Bioorg Med Chem. 2013 Jul 1;21(13):3839-49. doi: 10.1016/j.bmc.2013.04.022. Epub 2013 Apr 18.

Abstract

A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their intermediate ketones and indomethacin. The NO-donating oxime 6i revealed significant activity against renal cancer A498 cell lines with 50.52 cell growth inhibition.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Antineoplastic Agents / therapeutic use
  • Cell Line, Tumor
  • Edema / drug therapy
  • Humans
  • Kidney Neoplasms / drug therapy
  • Male
  • Nitric Oxide / administration & dosage
  • Nitric Oxide Donors / chemical synthesis
  • Nitric Oxide Donors / chemistry*
  • Nitric Oxide Donors / pharmacology*
  • Nitric Oxide Donors / therapeutic use
  • Oximes / chemical synthesis
  • Oximes / chemistry
  • Oximes / pharmacology
  • Oximes / therapeutic use
  • Rats
  • Stomach / drug effects
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology
  • Triazoles / therapeutic use
  • Ulcer / chemically induced

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents
  • Nitric Oxide Donors
  • Oximes
  • Triazoles
  • 1,2,4-triazole
  • Nitric Oxide