2,2',4-trihydroxybenzophenone: crystal structure, and anti-inflammatory and antioxidant activities

Chem Biodivers. 2007 Mar;4(3):488-99. doi: 10.1002/cbdv.200790041.

Abstract

The crystal structure of '2,2',4-trihydroxybenzophenone' (=(2,4-dihydroxyphenyl)(2-hydroxyphenyl)methanone; 1) was determined, and its molecular structure, along with intra- and intermolecular H-bonds, was analyzed. The anti-inflammatory potential of 1, evaluated by means of the rat-paw-edema assay, with carrageenan as inflammation stimulus, was found to be similar high as that of indomethacin. In contrast, benzophenone proper (2) was hardly active in this assay. Our results indicate that these anti-inflammatory effects are related to the action of kinins and prostaglandins. The radical-scavenging properties of 1 towards DPPH were found to be similar as those of typical phenolics, but somewhat lower than that of ascorbic acid. The structure-activity relationship (SAR) of 1 is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Antioxidants / therapeutic use
  • Benzophenones / chemistry*
  • Benzophenones / pharmacology
  • Benzophenones / therapeutic use
  • Crystallization
  • Edema / drug therapy
  • Edema / metabolism
  • Inflammation / drug therapy
  • Inflammation / metabolism
  • Male
  • Rats
  • Rats, Wistar

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antioxidants
  • Benzophenones