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

doi:10.1016/S0960-894X(00)00269-9

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 journal › Article › peer-review

26 Scopus citations

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 language	English (US)
Pages (from-to)	1443-1446
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1016/S0960-894X(00)00269-9
State	Published - Jul 3 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(00)00269-9

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AU - Johnson, Kenneth M.

AU - Kozikowski, Alan P.

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AB - 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.

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

Abstract

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