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1‐Ethyl‐1,4‐dihydro‐4‐oxo‐7‐(pyridinyl)‐3‐quinolinecarboxylic acids. II. Synthesis
Author(s) -
Carabateas Philip M.,
Brundage R. Pauline,
Gelotte Karl O.,
Gruett Monte D.,
Lorenz Roman R.,
Opalka Chester J.,
Singh Baldev,
Thielking William H.,
Williams Gordon L.,
Lesher George Y.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210655
Subject(s) - chemistry , quinoline , aniline , hydrolysis , pyridine , ring (chemistry) , ethyl ester , medicinal chemistry , organic chemistry , stereochemistry
The preparation of a variety of 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐pyridinyl‐3‐quinolinecarboxylic acids with a range of substituents on the pyridine ring is described. Starting with the appropriately substituted aniline and using the first two steps of the Gould‐Jacobs quinoline synthesis the 7‐pyridinyl‐3‐quinolinecarboxylates can be obtained. Ethylation at the 1‐position and hydrolysis of the ester group gives the desired acid products. These compounds have significant antibacterial activity: 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(4‐pyridinyl)‐3‐quinolinecarboxylic acid is now in clinical study and 7‐(2,6‐dimethyl‐4‐pyridinyl)‐1‐ethyl‐1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylic acid is under advanced evaluation.