ABSTRACT
First total synthesis of methylgerambullone (MGB, 1) isolated from Glycosmis angustifolia was completed via a convergent route. The effect of MGB on the contractile responses of the isolated guinea-pig ileum induced by acetylcholine was investigated. As a result, it showed a potent relaxation rate (78.66+/-4.30% at 100mg/L) in a concentration-dependent manner on longitudinal smooth muscle contraction of isolated guinea-pig ileum induced by 1microM acetylcholine.
Subject(s)
Acrylamides/chemical synthesis , Biological Products/chemical synthesis , Sulfones/chemical synthesis , Acetylcholine/pharmacology , Acrylamides/chemistry , Acrylamides/pharmacology , Animals , Biological Products/chemistry , Biological Products/pharmacology , Guinea Pigs , Ilium/drug effects , Muscle Relaxation/drug effects , Muscle, Smooth/drug effects , Rutaceae/chemistry , Sulfones/chemistry , Sulfones/pharmacologyABSTRACT
3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE(2) production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC(50)=0.61microM) of PGE(2) production.
