1983
DOI: 10.1021/jm00363a012
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Angiotensin converting enzyme inhibitors: 1-glutarylindoline-2-carboxylic acid derivatives

Abstract: 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.

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Cited by 72 publications
(35 citation statements)
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“…13, 137 Unlike the N-carboxyalkyl dipeptide series (Section IV.A), replacing proline with a bulky lipophilic surrogate, such as indoline-2(S)-carboxylic acid, in this series resulted in a 100-fold increase in activity (cf. 4-3 and 19-1).…”
Section: -9mentioning
confidence: 99%
“…13, 137 Unlike the N-carboxyalkyl dipeptide series (Section IV.A), replacing proline with a bulky lipophilic surrogate, such as indoline-2(S)-carboxylic acid, in this series resulted in a 100-fold increase in activity (cf. 4-3 and 19-1).…”
Section: -9mentioning
confidence: 99%
“…19 Aside from the above discussed hydrogenations, 1012,14,15,17 indolines can be synthesized by direct ring closure through amination reactions. 20 …”
mentioning
confidence: 99%
“…[30] BoraneϪdimethyl NMR (300 MHz, CDCl 3 ): δ ϭ 0.04 (s, 6 H), 0.89 (d, J ϭ 6.7 Hz, sulfide (4.4 mL, 0.044 mol) was added dropwise at 0°C to a solu-3 H), 0.90 (s, 9 H), 0.98 (d, J ϭ 6.7 Hz, 3 H), 1.12 (dt, J ϭ 13.5 tion of (2R*,4R*)-dimethyl glutarate. [31] After stirring for 3 h at and 7. . titioned between ether (20 mL) and aqueous saturated K 2 CO 3 solution (20 mL).…”
Section: (2s*3r*)-3-deuterio-4-methylpentan-2-ol (Deuterio-4)mentioning
confidence: 99%