Benzene‐di‐N‐substituted carbamates as conformationally constrained analogs of Pseudomonas lipase substrates

Abstract

AbstractBenzene‐1,2‐, ‐1,3‐, and ‐1,4‐di‐N‐substituted carbamates (1–15) are synthesized as the constrained analogs of gauche, eclipsed, and anti conformations of diesters of ethylene glycol, respectively. Carbamates 1–15 are characterized as the pseudo‐substrate inhibitors of Pseudomonas species lipase. Long‐chain carbamates are more potent inhibitors than short‐chain ones. Different geometries of benzene‐di‐substituted carbamates, such as benzene‐1,2‐di‐N‐octylcarbamate (3) (ortho compound), benzene‐1,3‐di‐N‐octylcarbamate (8) (meta compound), and benzene‐1,4‐di‐N‐octylcarbamate (13) (para compound), show similar inhibitory potencies for the enzyme. In other words, kinetic data suggest that the enzyme does not discriminate ortho, meta, and para geometries of these constrained analogs.