Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides as Antiprotozoal Agents

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Emanuel Hernández-NúñezGabriel Navarrete Vázquez


Parasitic diseases are a public health problem affecting millions of people worldwide. One of the scaffolds used in several drugs for the treatment of parasitic diseases is the benzimidazole moiety, a heterocyclic aromatic compound. This compound is a crucial pharmacophore group and is considered a privileged structure in medicinal chemistry. In this study, the benzimidazole core served as a model for the synthesis of a series of 2-(2-amino-5(6)-nitro-1H-benzimidazol-1-yl)-N-arylacetamides 1-8 as benznidazole analogues. The in silico pharmacological results calculated with PASS platform exhibited chemical structures highly similar to known antiprotozoal drugs. Compounds 1-8 when evaluated in silico for acute toxicity by oral dosing, were less toxic than benznidazole. The synthesis of compounds 1-8 were carried out through reaction of 5(6)-nitro-1H-benzimidazol-2-amine (12) with 2-chlroactemides 10a-h, in the presence of K₂CO₃ and acetonitrile as solvent, showing an inseparable mixture of two regioisomers with the -NO₂ group in position 5 or 6 with chemical yields of 60 to 94%. The prediction of the NMR spectra of molecule 1 coincided with the experimental chemical displacements of the regioisomers. Comparisons between the NMR p...Continue Reading


Dec 1, 2000·Bioinformatics·A LaguninV Poroikov
Mar 29, 2001·Journal of Pharmacological and Toxicological Methods·C A Lipinski
Jul 18, 2002·The Journal of Eukaryotic Microbiology·Roberto Cedillo-RiveraLilian Yépez-Mulia
Mar 4, 2003·Nature Reviews. Drug Discovery·Han van de Waterbeemd, Eric Gifford
Jun 18, 2003·Parasitology Research·W Raether, H Hänel
Aug 3, 2004·Nature Reviews. Drug Discovery·Ted T Ashburn, Karl B Thor
Apr 28, 2005·Mini Reviews in Medicinal Chemistry·Mariana Boiani, Mercedes Gonzalez
Nov 2, 2005·European Journal of Medicinal Chemistry·Gabriel Navarrete-VázquezFrancisco Hernández-Luis
Nov 23, 2005·European Journal of Medicinal Chemistry·Alice M R BernardinoVeronica F Amaral
May 26, 2006·Journal of Medicinal Chemistry·Mariana BoianiMercedes Gonzalez
Oct 2, 2007·Memórias do Instituto Oswaldo Cruz·Jean Jannin, Luis Villa
Nov 15, 2007·JAMA : the Journal of the American Medical Association·Caryn BernAnne C Moore
Feb 12, 2009·European Journal of Medicinal Chemistry·Emanuel Hernández-NúñezGabriel Navarrete-Vázquez
Feb 20, 2013·Journal of Agricultural and Food Chemistry·Yu-Bin BaiJin-Ming Gao
Mar 29, 2013·Journal of Environmental Science and Health. Part C, Environmental Carcinogenesis & Ecotoxicology Reviews·Nazanin G BakhtyariDouglas Young
Feb 18, 2014·Bioorganic & Medicinal Chemistry·Carlos Nava-ZuazoGabriel Navarrete-Vázquez
Mar 8, 2014·European Journal of Medicinal Chemistry·Monika GabaChander Mohan
May 16, 2014·The New England Journal of Medicine·Israel MolinaAlbert Pahissa
Dec 1, 2004·Drug Discovery Today. Technologies·Christopher A Lipinski
Dec 17, 2014·European Journal of Medicinal Chemistry·Digambar D GaikwadAbraham J Domb
Jan 9, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Yasser M ShakerHoda I El Diwani
Apr 8, 2015·International Journal for Parasitology·C M GuptaA A Sahasrabuddhe
Sep 8, 2015·Bioorganic & Medicinal Chemistry·Anelia Ts MavrovaAndrija Smelcerovic
Sep 17, 2015·Organic Letters·Yiding Chen, Michael C Willis
Dec 17, 2016·The Lancet Infectious Diseases·Usama Ramadan AbdelmohsenUte Hentschel


Feb 16, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Genaro Rocha-GarduñoGabriel Navarrete-Vázquez

Methods Mentioned

column chromatography
nuclear magnetic resonance

Related Concepts

Benzimidazole mononitrate
In Vivo NMR Spectroscopy
Drug Modeling
Inhibitory Concentration 50
Helminth Drug Sensitivity Tests
Analogs & derivatives
Antiprotozoal Agents

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