39650-64-1Relevant articles and documents
Study of the Effect of Substituents of ortho-Phenylenediamines in the Opening of Lactones and Lactams for Access to Benzimidazol-2-yl Alkanols and Benzimidazol-2-yl Alkylamines
Arimondo, Paola B.,Balleé, Alexia,Beaurain, Florian,Castillo-Aguilera, Omar,Depreux, Patrick,Goossens, Laurence
, p. 1216 - 1220 (2020/07/30)
Benzimidazoles represent common chemical moieties in bioactive compounds. The synthesis of this heterocycle often involves a condensation of an ortho-phenylenediamine with a carboxylic acid derivative. The observed dialkylation of the starting ortho-phenylenediamine is avoided by opening of lactones or lactams. This strategy can directly yield 1 H-benzimidazoles substituted at the 2-position by a functionalized chain. We present herein a study of the effect of different electron-withdrawing or electron-donating groups at the 4-position of ortho-phenylenediamines on the opening of lactones or lactams to synthesize benzimidazol-2-yl alkanols and benzimidazol-2-yl alkylamines.
A Developability-Focused Optimization Approach Allows Identification of in Vivo Fast-Acting Antimalarials: N -[3-[(Benzimidazol-2-yl)amino]propyl]amides
Keurulainen, Leena,Vahermo, Mikko,Puente-Felipe, Margarita,Sandoval-Izquierdo, Elena,Crespo-Fernández, Benigno,Guijarro-López, Laura,Huertas-Valentín, Leticia,De Las Heras-Due?a, Laura,Leino, Teppo O.,Siiskonen, Antti,Ballell-Pages, Lluís,Sanz, Laura M.,Casta?eda-Casado, Pablo,Jiménez-Díaz, M. Belén,Martínez-Martínez, María S.,Viera, Sara,Kiuru, Paula,Calderón, Félix,Yli-Kauhaluoma, Jari
supporting information, p. 4573 - 4580 (2015/06/25)
Malaria continues to be a major global health problem, being particularly devastating in the African population under the age of five. Artemisinin-based combination therapies (ACTs) are the first-line treatment recommended by the WHO to treat Plasmodium falciparum malaria, but clinical resistance against them has already been reported. As a consequence, novel chemotypes are urgently needed. Herein we report a novel, in vivo active, fast-acting antimalarial chemotype based on a benzimidazole core. This discovery is the result of a medicinal chemistry plan focused on improving the developability profile of an antichlamydial chemical class previously reported by our group. (Graph Presented).