6533b826fe1ef96bd1284fd4

RESEARCH PRODUCT

ChemInform Abstract: 2-Aryl-Substituted 4H-3,1-Benzoxazin-4-ones as Novel Active Substances for the Cardiovascular System.

U. Rose

subject

BenzoxazinonesStereochemistryArylHalogenationchemistry.chemical_elementIleumGeneral MedicineCalciumPhosphonatechemistry.chemical_compoundmedicine.anatomical_structurechemistryIn vivoCirculatory systemmedicine

description

4H-3,1-Benzoxazin-4-ones of the structural types 3 and 4 are accessible by cyclization reactions. The introduction of the phosphonate group was achieved by way of Wohl-Ziegler bromination and subsequent Michaelis-Arbuzow reaction with a trialkyl phosphite. Pharmacological investigations on isolated left atria, ileum specimens, and Langendorff hearts as well as in vivo circulatory studies on anesthetized rats revealed that the phosphonates 4 exert calcium antagonistic effects. Whereas 2-(arylvinyl)benzoxazinones gave rise to pronounced negative inotropic effects, compound 3e exhibited relaxing effects on smooth musculature in particular and markedly increased the coronary flow through Langendorff hearts.

https://doi.org/10.1002/chin.199220220