The preparation of a series of 1-glutarylindoline-2(S)-carboxylic acid derivatives, 6a-v and 21a-c, is described. The above compounds were tested for inhibition of angiotensin converting enzyme. The structure-activity relationship of the series is also discussed. Compound 6u, the most potent member of the series, had an in vitro IC50 of 4.8 X 10(-9) M. Compound 6v, an ethyl ester of 6u, lowered blood pressure 70 mm in spontaneous hypertensive rats at an oral dose of 30 mg/kg.
Vol. 28 ml. of absolute ethanol. The autoclave was then shaken under 1,000 lb. of hydrogen pressure at 100°for 1 hr.After filtration, the solution was concentrated in vacuo and the oily residue taken up in ether and separated into basic and neutral fractions. The basic fraction was converted to its hydrochloride salt and recrystallized from ethanol-ether to give 5.8 g. (50%) of analytically pure ethyl a-diphenvlmethyI-0-alaninate hydro-
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