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- Title
Molecular structure of a brominated 2-benzazepinone - a crucial intermediate in the synthesis of novel chemokine CCR2 receptor antagonists.
- Authors
Kokornaczyk, Artur K.; Thum, Simone; Daniliuc, Constantin G.; Junker, Anna; Wünsch, Bernhard
- Abstract
Chemokines (chemoattractant cytokines) together with their receptors represent key players in inflammatory processes. In order to develop novel chemokine CCR2 and CCR5 receptor antagonists, 2-benzazepin-1-one 5 was prepared, which showed promising CCR2 affinity. During the synthesis, regioisomeric bromo substituted ß-keto esters 4a and 4b had to be separated. A crystal structure determination of the regioisomer 4b displayed unequivocally the bromine atom in the 7-position and the existence of 4b as the enol ester tautomer. Although the 7-membered azepine ring is rather flat, it is distorted around the 3-methylene moiety.
- Subjects
BENZENE compound synthesis; MOLECULAR structure; CHEMOKINE receptors; CHEMICAL inhibitors; INFLAMMATION
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2017, Vol 72, Issue 6, p421
- ISSN
0932-0776
- Publication type
Article
- DOI
10.1515/znb-2017-0030