Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter

K. R C Prakash, Gian Luca Araldi, Miles P. Smith, Mai Zhang, Kenneth M. Johnson, Alan P. Kozikowski

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

In our search for novel therapeutic agents useful in the treatment of cocaine abuse, we have studied the synthesis and biological activity of 2β- butyl-3-phenyltropane derivatives with the phenyl ring in α- or β- configuration and bearing different substituents at the 6- and 7-positions of the tropane ring. All of the compounds synthesized showed micromolar or submicromolar affinity for the DAT in the rat striatum. In particular, among all the compounds described in this paper, the 7α-fluoro-3α-phenyltropane derivative 12 was found to be the most potent, inhibiting mazindol binding with a K(i) of 0.20 μM and dopamine reuptake with a K(i) of 0.49 μM.

Original languageEnglish (US)
Pages (from-to)43-58
Number of pages16
JournalMedicinal Chemistry Research
Volume8
Issue number1-2
StatePublished - 1998

Fingerprint

Mazindol
Tropanes
Cocaine-Related Disorders
Dopamine Plasma Membrane Transport Proteins
Bioactivity
Dopamine
Bearings (structural)
Ligands
Derivatives
Cocaine
Rats
Therapeutics

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery

Cite this

Prakash, K. R. C., Araldi, G. L., Smith, M. P., Zhang, M., Johnson, K. M., & Kozikowski, A. P. (1998). Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter. Medicinal Chemistry Research, 8(1-2), 43-58.

Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter. / Prakash, K. R C; Araldi, Gian Luca; Smith, Miles P.; Zhang, Mai; Johnson, Kenneth M.; Kozikowski, Alan P.

In: Medicinal Chemistry Research, Vol. 8, No. 1-2, 1998, p. 43-58.

Research output: Contribution to journalArticle

Prakash, KRC, Araldi, GL, Smith, MP, Zhang, M, Johnson, KM & Kozikowski, AP 1998, 'Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter', Medicinal Chemistry Research, vol. 8, no. 1-2, pp. 43-58.
Prakash, K. R C ; Araldi, Gian Luca ; Smith, Miles P. ; Zhang, Mai ; Johnson, Kenneth M. ; Kozikowski, Alan P. / Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter. In: Medicinal Chemistry Research. 1998 ; Vol. 8, No. 1-2. pp. 43-58.
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