Synthesis, Lipophilicity and Structure of 2,5-Disubstituted 1,3,5-Dithiazine Derivatives

Leyte Winfield, Chunming Zhang, Christy A. Reid, Edwin D. Stevens, Mark L. Trudell, Sari E Izenwasser, Dean Wade

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)827-832
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume40
Issue number5
StatePublished - Sep 1 2003

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Derivatives
Dopamine Uptake Inhibitors
Dopamine Plasma Membrane Transport Proteins
Crystal structure
X rays
vanoxerine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Winfield, L., Zhang, C., Reid, C. A., Stevens, E. D., Trudell, M. L., Izenwasser, S. E., & Wade, D. (2003). Synthesis, Lipophilicity and Structure of 2,5-Disubstituted 1,3,5-Dithiazine Derivatives. Journal of Heterocyclic Chemistry, 40(5), 827-832.

Synthesis, Lipophilicity and Structure of 2,5-Disubstituted 1,3,5-Dithiazine Derivatives. / Winfield, Leyte; Zhang, Chunming; Reid, Christy A.; Stevens, Edwin D.; Trudell, Mark L.; Izenwasser, Sari E; Wade, Dean.

In: Journal of Heterocyclic Chemistry, Vol. 40, No. 5, 01.09.2003, p. 827-832.

Research output: Contribution to journalArticle

Winfield, L, Zhang, C, Reid, CA, Stevens, ED, Trudell, ML, Izenwasser, SE & Wade, D 2003, 'Synthesis, Lipophilicity and Structure of 2,5-Disubstituted 1,3,5-Dithiazine Derivatives', Journal of Heterocyclic Chemistry, vol. 40, no. 5, pp. 827-832.
Winfield, Leyte ; Zhang, Chunming ; Reid, Christy A. ; Stevens, Edwin D. ; Trudell, Mark L. ; Izenwasser, Sari E ; Wade, Dean. / Synthesis, Lipophilicity and Structure of 2,5-Disubstituted 1,3,5-Dithiazine Derivatives. In: Journal of Heterocyclic Chemistry. 2003 ; Vol. 40, No. 5. pp. 827-832.
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AU - Wade, Dean

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