SAR studies of piperidine-based analogues of cocaine. Part 3: Oxadiazoles

Pavel A. Petukhov, Mei Zhang, Kenneth J. Johnson, Srihari R. Tella, Alan P. Kozikowski

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The synthesis of novel 4β-aryl-1-methyl-3α-(3-substituted-1,2,4-oxadiazol-5-yl) piperidines, bioisosteres of ester (+)-1, is described. The synthesized oxadiazoles were evaluated for their affinity to the DAT and their ability to inhibit monoamine reuptake at the DAT, NET, and 5HTT. The results show that affinity to the DAT and ability to inhibit the reuptake at the DAT, NET, and 5HTT is a function of the size of the substituent in the oxadiazole ring. (+)-(3R,4S)-4β-(4-Chlorophenyl)-1-methyl-3α-(3-methyl-1,2,4- oxadiazol-5-yl)piperidine [(+)-2a], which is structurally and pharmacologically most similar to the ester (+)-1 in this series, showed at least a 2-fold longer duration of action when compared to ester (+)-1.

Original languageEnglish (US)
Pages (from-to)2079-2083
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume11
Issue number16
DOIs
StatePublished - Aug 20 2001

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Oxadiazoles
Cocaine
Esters
Piperidines
piperidine

ASJC Scopus subject areas

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

Cite this

Petukhov, P. A., Zhang, M., Johnson, K. J., Tella, S. R., & Kozikowski, A. P. (2001). SAR studies of piperidine-based analogues of cocaine. Part 3: Oxadiazoles. Bioorganic and Medicinal Chemistry Letters, 11(16), 2079-2083. https://doi.org/10.1016/S0960-894X(01)00379-1

SAR studies of piperidine-based analogues of cocaine. Part 3 : Oxadiazoles. / Petukhov, Pavel A.; Zhang, Mei; Johnson, Kenneth J.; Tella, Srihari R.; Kozikowski, Alan P.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 11, No. 16, 20.08.2001, p. 2079-2083.

Research output: Contribution to journalArticle

Petukhov, PA, Zhang, M, Johnson, KJ, Tella, SR & Kozikowski, AP 2001, 'SAR studies of piperidine-based analogues of cocaine. Part 3: Oxadiazoles', Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 16, pp. 2079-2083. https://doi.org/10.1016/S0960-894X(01)00379-1
Petukhov, Pavel A. ; Zhang, Mei ; Johnson, Kenneth J. ; Tella, Srihari R. ; Kozikowski, Alan P. / SAR studies of piperidine-based analogues of cocaine. Part 3 : Oxadiazoles. In: Bioorganic and Medicinal Chemistry Letters. 2001 ; Vol. 11, No. 16. pp. 2079-2083.
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