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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
agricultural and biological sciences
Nature-inspired indolyl-2-azabicyclo[2.2.2]oct-7-ene derivatives as promising agents for the attenuation of withdrawal symptoms: Synthesis of 20-desethyl-20-hydroxymethyl-11-demethoxyibogaine
Natural Product Research, Volume 20, No. 8, Year 2006
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Description
Microwave assisted Diels-Alder cycloaddition of 5-Br-N -benzylpyridinone (2) with methyl acrylate is described to gain an easy access to 7-bromo-2-benzyl-3-oxo-2-aza-5 or 6-carbomethoxy bicyclo[2.2.2]oct-7-enes (3)-(6). The preparation of the ibogaine analogue 20-desethyl-(20-endo)-hydroxymethyl-11-demethoxyibogaine (17) is described by stereoselective hydrogenation of the C(7)-C(8) double bond. Biological evaluation showed an interesting in vitro binding profile toward dopamine transporter, serotonin transporter and opioid receptor systems accompanied by an antiwithdrawal effect in mice for hydroxymethyl 7-indolyl-2-aza-bicyclo[2.2.2]oct-2-ene (14). The simplification of the ibogaine structure appears as a promising approach toward the design of compounds that could reduce the withdrawal symptoms. © 2006 Taylor & Francis.
Authors & Co-Authors
Passarella, Daniele
Italy, Milan
Università Degli Studi Di Milano
Barilli, A.
Italy, Milan
Università Degli Studi Di Milano
Efange, Simon Mbua Ngale
Cameroon, Buea
Université de Buea
Elisabetsky, Elaine
Brazil, Porto Alegre
Universidade Federal do Rio Grande do Sul
Leal, Mirna Bainy
Brazil, Porto Alegre
Pontifícia Universidade Católica do Rio Grande do Sul
Brazil, Porto Alegre
Universidade Federal do Rio Grande do Sul
Lesma, G.
Italy, Milan
Università Degli Studi Di Milano
Linck, V. M.
Brazil, Porto Alegre
Pontifícia Universidade Católica do Rio Grande do Sul
Mash, D. C.
United States, Miami
University of Miami Leonard M. Miller School of Medicine
Martinelli, M.
Italy, Baranzate
Nikem Research S.r.l.
Peretto, I.
Italy, Baranzate
Nikem Research S.r.l.
Silvani, A.
Italy, Milan
Università Degli Studi Di Milano
Danieli, Bruno
Italy, Milan
Università Degli Studi Di Milano
Statistics
Citations: 12
Authors: 12
Affiliations: 6
Identifiers
Doi:
10.1080/14786410500160645
ISSN:
14786419
e-ISSN:
14786427
Research Areas
Health System And Policy