Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents

This is the first report on aurones as a new class of drugs with anti-inflammatory and antimicrobial agents. A series of 2,2-bisaminomethylated aurone analogues (4a–j) were synthesized by Mannich reaction from 1,3,5-trimethoxybenzene in three steps. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR and mass spectral analysis. All the synthesized compounds were screened against the pro-inflammatory cytokines (TNF-α, IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 4a, 4b, 4c, 4d, and 4e showed promising results against IL-6 at 10 μM concentration (74–100%). Compounds 4a, 4b and 4c were found to be active against TNF-α (76–100%) at 10 μM. Interestingly, all compounds have shown good antimicrobial activity. Compounds 4d, 4e and 4f showed excellent antimicrobial activity as compared with standard drugs.

Graphical abstractA novel series of 2,2-bisaminomethylated aurone analogues have been synthesized by Mannich reaction. The compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and antimicrobial activity.Figure optionsDownload full-size imageDownload as PowerPoint slide