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Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond.

Abstract：

:The synthesis of five amino phosphorus derivatives, 1a-e, is described. The derivatives were incorporated into a series (18) of analogues of the 5-14 portion of angiotensinogen, in most cases at the scissile Leu-Val bond. The resultant compounds were tested in vitro for their ability to inhibit human plasma renin. Replacement of the scissile bond with the phosphinic analogue of Leu10-Val11 (1b) gave the most potent inhibitors, having IC50 = 7.5 x 10(-8) M for H-Pro-His-Pro-Phe-His-(1b)-Ile-His-Lys-OH and IC50 = 1.0 x 10(-7) M for Z-Arg-Arg-Pro-Phe-His-(1b)-Ile-His-NH2. The shorter phosphonic acid sequence Z-Pro-Phe-His-(1d) retained biological activity with an IC50 = 6.4 x 10(-6) M.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Allen MC,Fuhrer W,Tuck B,Wade R,Wood JM

doi

10.1021/jm00127a041

subject

Has Abstract

pub_date

1989-07-01 00:00:00

pages

1652-61

issue

7

eissn

0022-2623

issn

1520-4804

journal_volume

32

pub_type

杂志文章

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