Synthesis of 2-{[2-(2-oxo-1-azacycloalkyl)acetamido]phenoxy}acetic acids and their activity as aminopeptidase M inhibitors

Abstract

A series of 9 phenoxyacetic acids substituted in the o-, m-, and p-position of benzene ring with 2-(2-oxo-1-azacycloalkyl)acetamidic moiety containing 5–7-membered w-lactam ring was prepared by a 4-step synthetic pro¬cedure. Five selected substances of this series were tested in vitro for inhibition of porcine kidney aminopeptidase M. 2-{4-[2-(2-Oxoperhydroazepin-1-yl)acetamido]phenoxy}acetic acid exhibited the highest activity with Ki = 243.6 mM.

Keywords

• w-lactams
• phenoxyacetic acids
• aminopeptidase M
• inhibition