Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency

Abstract

The current research effort focuses on dehydrozingerone (DHZ, 1), a secondary metabolite discovered in the rhizome of Zingiber officinale. Here, we designed and synthesized the diaryl ether derivatives in high yields (80–93%) using substituted arylboronic acids and copper-promoted arylation of phenol. For anti-microbial activity against clinically significant infectious strains of Mycobacterium tuberculosis (ATCC 27294) and H37Ra (ATCC 25177), as well as against Gram-positive and Gram-negative bacteria (B. subtilis ATCC 6633, E. faecalis ATCC 29212, P. aeruginosa ATCC 9027, Escherichia coli ATCC 11105). 16 g/ml MIC value and mycobacterial potential. Compound 7 was the most active of all the compounds, with a MIC Value of 4 g/ml. Additionally, pro-inflammatory cytokines were checked for across the board in the compounds (1–16). IL6 and TNF- are produced by LPS-stimulated RAW 264.7 cells in a dose-dependent manner.

Keywords

• Dehydrozingerone
• Copper-promoted arylation
• Diaryl derivatives
• Anti-tubercular and anti-inflammatory activity