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Compounds with Positive Inotropic Activity, IV: Synthesis of N‐Methoxyquinolinium Salts and Their Effects in Heart Muscles
Author(s) -
Bünz Claudia,
Heber Dieter,
Ravens Ursula
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933260410
Subject(s) - chemistry , inotrope , nitration , quinoline , substituent , nucleophile , nitro , medicinal chemistry , biological activity , alkylation , nucleophilic substitution , stereochemistry , organic chemistry , in vitro , medicine , biochemistry , catalysis , alkyl
N ‐Methoxyquinolinium salts 3 are prepared as potential cardiotonic agents by alkylation of the corresponding N ‐oxides 2 synthesized by two different methods. 1. Oxidation of some quinoline derivatives 1 using 30% H 2 O 2 or 3‐chloroperbenzoic acid. 2. Nitration of the quinoline‐ N ‐oxides 2a, 2c , and 2m . Preparation of 2h and 2k requires subsequent nucleophilic ipso ‐substitution of the nitro group. The compounds 3 are tested for positive inotropic activity on isolated left atria and papillary muscles from guinea‐pig. Structure activity relationships indicate that the effect depends on the N ‐methoxy group of the target compounds as well as on the presence of an electron‐withdrawing substituent.