Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/13535
Title: Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies
Authors: Gopi, Elumalai
Kumar, Tarun
Menna Barreto, Rubem F. S.
Valença, Wagner O.
Silva Júnior, Eufrânio N. da
Namboothir, Irishi N. N.
Affilliation: Indian Institute of Technology Bombay. Department of Chemistry. Mumbai, India.
Indian Institute of Technology Bombay. Department of Chemistry. Mumbai, India.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ, Brasil.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.
Indian Institute of Technology Bombay. Department of Chemistry. Mumbai, India.
Abstract: Cascade reactions of amidines with nitroallylic acetates and α-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.
Keywords: Imidazoles
Nitroallylic acetates
Amidines
Trypanocidal activity
α-bromonitroalkenes
DeCS: Imidazóis
Acetatos
Tripanossomicidas
Amidinas
Issue Date: 2015
Publisher: Royal Society of Chemistry
Citation: GOPI, Elumalai; et al. Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies. Org. Biomol. Chem., v.13, p.9862-9871, Aug. 2015.
DOI: 10.1039/c5ob01444a
ISSN: 1477-0520
Copyright: open access
Appears in Collections:IOC - Artigos de Periódicos

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