Design, synthesis, characterization and in vitro and in vivo anti-inflammatory evaluation of novel pyrazole-based chalcones

Abstract

A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D ¹H–¹H COSY, ¹H–¹³C HSQC and ¹H–¹³C HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

• Anti-inflammatory activity
• chalcone
• COSY
• HMBC
• HSQC
• pyrazole

Declaration of interest

The authors report no conflicts of interest. The authors alone are responsible for the content and writing of this article. Author Hemant V. Chavan is thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, Govt. of India, for financial support in the form of SRF.

Supplementary material available online