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    Organometallic benzimidazoles: Synthesis, characterization and antimalarial activity

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    et al.A series of ferrocenyl and cyrhetrenyl benzimidazoles were synthesized and characterized. The condensation-cyclization reaction of cyrhetrenecarbaldehyde with 1,2-phenylendiamine or 4-nitro-1,2-phenylendiamine produces only the 2-cyrhetrenyl-benzimidazoles [1-Re-(H, NO2)] whereas with the same diamines, ferrocenecarbaldehyde yields two products: 2-ferrocenyl-benzimidazole [1-Fe-(H, NO2)] and N-ferrocenylmethyl-2-ferrocenyl-benzimidazole [2-Fe-(H, NO2)]. The structures of all products were confirmed by 1H, 13C NMR spectra and MS. The molecular structure of 2-Fe-NO2 was determined by single crystal X-ray analysis. The antimalarial evaluation studies against the CQ susceptible-strain (3D7) and the CQ resistant-strain (W2) of Plasmodium falciparum revealed cyrhetrene conjugates to be most potent of the tested compounds. The presence of the nitro group at the 5-position of organometallic-benzimidazoles [1-M (M = Re, Fe)] also increases the antimalarial activity. © 2013 Elsevier B.V.A.H.K. acknowledges FONDECYT-Chile (Project 1110669) and D.I. Pontificia Universidad Católica de Valparaíso. R.A. acknowledges MECESUP and CONICYT for Doctoral scholarship and D.I.-PUCV and FONDECYT-Chile (Project 3120091) for Postdoctoral position. The Ministry of Defense (Délégation Générale pour l'Armement and the Direction Centrale du Service de Santé des Armées, grant no. 10co405) is acknowledged for funding of P. falciparum screening.Peer Reviewe
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