Structure-activity relationship studies of N-sulfonyl analogs of cocaine: Role of ionic interaction in cocaine binding

Alan P. Kozikowski, M. K Eddine Saiah, John S. Bergmann, Kenneth M. Johnson

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Six new N-sulfonylated analogs of cocaine have been prepared, and these compounds have been evaluated for their ability to inhibit [3H]mazindol binding and [3H]dopamine uptake into striatal synaptosomes. The N-sulfonyl compounds still inhibited binding and uptake at low micromolar concentrations despite the neutral character of the tropane nitrogen, thus suggesting that the binding of cocaine to the dopamine transporter may not require protonation of its nitrogen and ionic interaction with its recognition site.

Original languageEnglish (US)
Pages (from-to)3440-3442
Number of pages3
JournalJournal of Medicinal Chemistry
Volume37
Issue number20
StatePublished - 1994

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Structure-Activity Relationship
Cocaine
Nitrogen
Mazindol
Tropanes
Corpus Striatum
Dopamine Plasma Membrane Transport Proteins
Synaptosomes
Protonation
Dopamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kozikowski, A. P., Saiah, M. K. E., Bergmann, J. S., & Johnson, K. M. (1994). Structure-activity relationship studies of N-sulfonyl analogs of cocaine: Role of ionic interaction in cocaine binding. Journal of Medicinal Chemistry, 37(20), 3440-3442.

Structure-activity relationship studies of N-sulfonyl analogs of cocaine : Role of ionic interaction in cocaine binding. / Kozikowski, Alan P.; Saiah, M. K Eddine; Bergmann, John S.; Johnson, Kenneth M.

In: Journal of Medicinal Chemistry, Vol. 37, No. 20, 1994, p. 3440-3442.

Research output: Contribution to journalArticle

Kozikowski, Alan P. ; Saiah, M. K Eddine ; Bergmann, John S. ; Johnson, Kenneth M. / Structure-activity relationship studies of N-sulfonyl analogs of cocaine : Role of ionic interaction in cocaine binding. In: Journal of Medicinal Chemistry. 1994 ; Vol. 37, No. 20. pp. 3440-3442.
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