2,2',4-trihydroxybenzophenone: crystal structure, and anti-inflammatory and antioxidant activities.
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.
Doriguetto
Antônio C
AC
Laboratório de Cristalografia, Departamento de Ciências Exatas, Universidade Federal de Alfenas-UNIFAL-MG, Rua Gabriel Monteiro da Silva, 714, Alfenas-MG, 37130-000 Brazil. doriguetto@unifal-mg.edu.br
Martins
Felipe T
FT
Ellena
Javier
J
Salloum
Rogério
R
dos Santos
Marcelo H
MH
Moreira
Maria E C
ME
Schneedorf
José M
JM
Nagem
Tanus J
TJ
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D001577:Benzophenones / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D003460:Crystallization; D004487:Edema / Q000188:drug therapy / Q000378:metabolism; D007249:Inflammation / Q000188:drug therapy / Q000378:metabolism; D008297:Male; D051381:Rats; D017208:Rats, Wistar
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D001577:Benzophenones