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

A series of 9 phenoxyacetic acids substituted in the o-, m-, and p-po- sition of benzene ring with 2-(2-oxo-1-azacycloalkyl)acetamidic moiety con- taining 5-7-membered -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)acet- amido)phenoxy}acetic acid exhibited the highest activity with Ki = 243.6 M.