An enantioselective synthesis and biobehavioral evaluation of 7-fluoro-3-(p-fluorophenyl)-2-propyltropanes

K. R C Prakash, Monika Trzcinska, Kenneth M. Johnson, Alan P. Kozikowski

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Optically pure 7-fluorotropanes 3a-c, were synthesized as structural probes of the dopamine transporter. The synthesis of these compounds was accomplished through the asymmetric 1,3-dipolar cycloaddition reaction of the oxidopyridinium betaine 4 with the chiral dipolarophile (R)-p-tolyl vinyl sulfoxide. In the preliminary analysis, tropane 3a was found to reduce the rewarding effects of cocaine in the brain stimulation reward paradigm. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original languageEnglish (US)
Pages (from-to)1443-1446
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume10
Issue number13
DOIs
StatePublished - Jul 3 2000

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sulfoxide
Tropanes
Betaine
Dopamine Plasma Membrane Transport Proteins
Cycloaddition
Cycloaddition Reaction
Reward
Cocaine
Brain

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

An enantioselective synthesis and biobehavioral evaluation of 7-fluoro-3-(p-fluorophenyl)-2-propyltropanes. / Prakash, K. R C; Trzcinska, Monika; Johnson, Kenneth M.; Kozikowski, Alan P.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 10, No. 13, 03.07.2000, p. 1443-1446.

Research output: Contribution to journalArticle

Prakash, K. R C ; Trzcinska, Monika ; Johnson, Kenneth M. ; Kozikowski, Alan P. / An enantioselective synthesis and biobehavioral evaluation of 7-fluoro-3-(p-fluorophenyl)-2-propyltropanes. In: Bioorganic and Medicinal Chemistry Letters. 2000 ; Vol. 10, No. 13. pp. 1443-1446.
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