Ibogaine analogues. Synthesis and preliminary pharmacological evaluation of 7-heteroaryl-2-azabicyclo[2.2.2]oct-7-enes

Daniele Passarella; Raffaele Favia; Alessandra Giardini; Giordano Lesma; Marisa Martinelli; Alessandra Silvani; Bruno Danieli; Simon M N Efange; Deborah C Mash

doi:10.1016/s0968-0896(02)00524-2

Ibogaine analogues. Synthesis and preliminary pharmacological evaluation of 7-heteroaryl-2-azabicyclo[2.2.2]oct-7-enes

Bioorg Med Chem. 2003 Mar 20;11(6):1007-14. doi: 10.1016/s0968-0896(02)00524-2.

Authors

Daniele Passarella¹, Raffaele Favia, Alessandra Giardini, Giordano Lesma, Marisa Martinelli, Alessandra Silvani, Bruno Danieli, Simon M N Efange, Deborah C Mash

Affiliation

¹ Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milan, Italy. [email protected]

PMID: 12614886
DOI: 10.1016/s0968-0896(02)00524-2

Abstract

Synthesis of 7-heteroaryl-2-azabicyclo[2.2.2]oct-7-enes by cycloaddition and subsequent cross-coupling reaction is described. Binding affinity of these novel compounds towards the characteristic receptorial targets of ibogaine is illustrated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemical synthesis*
Alkenes / pharmacology*
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
Cyclization
Ibogaine / analogs & derivatives*
Ibogaine / pharmacology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Radioligand Assay
Receptors, Drug / drug effects

Substances

Alkenes
Bridged Bicyclo Compounds, Heterocyclic
Indicators and Reagents
Receptors, Drug
Ibogaine