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Synthesis, lipophilicity and structure of 2,5-disubstituted 1, 3, 5-dithiazine derivatives

✍ Scribed by Leyte Winfield; Chunming Zhang; Christy A. Reid; Edwin D. Stevens; Mark L. Trudell; Sari Izenwasser; Dean Wade

Publisher: Journal of Heterocyclic Chemistry
Year: 2003
Tongue: English
Weight: 72 KB
Volume: 40
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570400512

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✦ Synopsis

Abstract

A series of 2,5‐disubstituted 1,3,5‐dithiazine derivatives were synthesized as potential analogues of the potent dopamine uptake inhibitor GBR 12909. The lipophilic character of the 1,3,5‐dithiazine derivatives were experimentally (log P) and computationally (clog P) determined. The in vitro binding affinities of the 2,5‐disubstituted 1,3,5‐dithiazine derivatives at the dopamine transporter were determined to be much less potent than the binding affinity of GBR 12909 due to steric and electronic effects inherent to the 1,3,5‐dithiazine ring system. The X‐ray crystal structure of 2‐(2‐[bis(4‐fluorophenyl)methoxy]ethyl)‐5‐(3‐phenylpropyl)‐1,3,5‐dithiazine (7) revealed that the 5‐(3‐phenylpropyl) group is in a pseudo‐axial orientation and syn to the 2‐ethoxybenzhydryl moiety.

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