0000000000620122
AUTHOR
Rose U
Synthesis, configuration, and calcium modulatory properties of enantiomerically pure 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates.
Enantiomerically pure hexahydroquinolinones of the structural type 9 were prepared by a variation of the Hantzsch synthesis in which an optically active acetoacetate served as a chiral auxiliary reagent. Determinations of the de and ee values are described. The absolute configurations of the optically pure products were characterized by single-crystal X-ray analysis. The antipodes 9a and 9b exhibited calcium antagonistic activities on smooth musculature; the (S)-(-)-enantiomer 9b was the more potent compound with regard to the EC50 values which differed by a factor of 100; the intrinsic activity of 9b was 1.2, compared with a value of 0.54 for 9a. On the other hand, R-(+)-9a exerted positiv…
ChemInform Abstract: Vinylogous and Coupled Hexahydroquinolinones and Dihydropyridines with Calcium-Modulating Effects.
The vinylogous, anellated and non-anellated dihydropyridines 4 and their coupled analogues 5 are accessible through Hantzsch-type cyclization reactions. IR, 1H-NMR, and mass spectral data are in agreement with the postulated structures. Pharmacological investigations on electrically-stimulated left atria of guinea pigs with some of the compounds gave rise to positive inotropic activities whereas BaCl2-induced contractions of the ileum were inhibited in a dose-dependent manner by some of the products.