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 microM.
Lee
Su-Lin
SL
School of Pharmacy, College of Medicine, National Taiwan University, Taipei 100, Taiwan, ROC.
Huang
Wei-Jan
WJ
Lin
Wan Wan
WW
Lee
Shoei-Sheng
SS
Chen
Chung-Hsiung
CH
D000588:Amines / Q000138:chemical synthesis* / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001681:Biological Assay; D051546:Cyclooxygenase 2 / Q000187:drug effects; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D036381:Diarylheptanoids / Q000494:pharmacology; D006536:Heptanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008264:Macrophages / Q000187:drug effects; D015394:Molecular Structure; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors
D000588:Amines; D000893:Anti-Inflammatory Agents; D052246:Cyclooxygenase 2 Inhibitors; D036381:Diarylheptanoids; D006536:Heptanes; C409456:oregonin; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2