Cardiac-slowing amidines containing the 3-thioindone group. Potential antianginal agents.

Abstract:

:A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

journal_name

J Med Chem

authors

Zelesko MJ,McComsey DF,Hageman WE,Nortey SO,Baker CA,Maryanoff BE

doi

10.1021/jm00356a021

subject

Has Abstract

pub_date

1983-02-01 00:00:00

pages

230-7

issue

2

eissn

0022-2623

issn

1520-4804

journal_volume

26

pub_type

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