Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs

Seven diarylheptylamine (12a–g) and four diarylheptanoid analogs (3–5, 9), structurally related to the natural anti-inflammatory agent oregonin (1), have been prepared from curcumin (2) for evaluation of their activity against the expression of iNOS and COX-2. Diarylheptylamine 12b and diarylheptanoid analogs can inhibit iNOS and COX-2 responses of LPS, although less potently than 1. These compounds, however, possess stronger potency than 1 against COX-2-derived PGE2 formation, of which hexahydrocurcumin (4) is the most potent one with an IC50 value of 0.7 μM.

Analogs inhibit iNOS and COX-2 responses of LPS in macrophages and also exhibit marked inhibition of COX-2-derived PGE2 formation.Figure optionsDownload as PowerPoint slide