The preparation of a series of 1, 4-thiazepine-2, 5-diones, 14-thiazine-2, 5-diones, and 1, 4- benzothiazepine-2, 5-diones and their ability in inhibiting the activity of angiotensin- converting enzyme (ACE) in vitro and in vivo were examined. These compounds are assumed to act as prodrugs since they undergo rapid ring-opening reactions to give the corresponding biologically active free SH compounds when incubated with rat plasma or ...