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Imidazoles from nitroallylic acetates and alpha-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies

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Title Imidazoles from nitroallylic acetates and alpha-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies
 
Creator GOPI, E
KUMAR, T
MENNA-BARRETO, RFS
VALENCA, WO
DA SILVA, EN
NAMBOOTHIRI, INN
 
Subject MORITA-BAYLIS-HILLMAN
MBH-TYPE REACTION
THIOUREA-TERTIARY AMINE
RETRACTED ARTICLE. SEE
ONE-POT SYNTHESIS
CASCADE REACTIONS
ENANTIOSELECTIVE SYNTHESIS
ORGANOCATALYTIC SYNTHESIS
HETEROCYCLIC-DERIVATIVES
REGIOSELECTIVE SYNTHESIS
 
Description Cascade reactions of amidines with nitroallylic acetates and alpha-bromonitroalkenes provide potentially bioactive imidazoles in good to excellent yields in most cases. While 2,4-disubstituted imidazol-5-yl acetates are formed in the first case, 2,4-disubstituted imidazoles, bearing no substituent at position 5, are the products in the second case. These two series of imidazoles, viz. 2,4,5-trisubstituted and 2,4-disubstituted, were screened for their activity against the protozoan parasite Trypanosoma cruzi which is responsible for Chagas disease. As many as three compounds were as active as the standard benznidazole and two others were 2-3-fold more active highlighting the potential of substituted imidazoles, easily accessible from nitroalkenes, as possible anti-parasitic agents.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:14:59Z
2016-01-15T07:14:59Z
2015
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 13(38)9862-9871
1477-0520
1477-0539
http://dx.doi.org/10.1039/c5ob01444a
http://dspace.library.iitb.ac.in/jspui/handle/100/18024
 
Language en