Abstract:
: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.
journal_name
Nat Prod Resjournal_title
Natural product researchauthors
Passarella D,Barilli A,Efange SM,Elisabetsky E,Leal MB,Lesma G,Linck VM,Mash DC,Martinelli M,Peretto I,Silvani A,Danieli Bdoi
10.1080/14786410500160645subject
Has Abstractpub_date
2006-07-10 00:00:00pages
758-65issue
8eissn
1478-6419issn
1478-6427pii
L0X2Q5V68183W5U7journal_volume
20pub_type
杂志文章abstract::Alternanthera brasiliana is popularly known as 'penicillin' and used as an anti-inflammatory and for wound healing. The objective of this work was the phytochemical study of the species by analytical techniques such as LC-MS/MS and GC-MS. Twenty-seven compounds were identified, five by LC-MS and 22 by GC-MS analysis. ...
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