116248-38-5Relevant academic research and scientific papers
Rapid synthesis of new 5-nitroimidazoles as potential antibacterial drugs via VNS procedure
Crozet, Maxime D.,Remusat, Vincent,Curti, Christophe,Vanelle, Patrice
, p. 3639 - 3646 (2006)
Original 4-arylsulfonylmethyl-5-nitroimidazoles were prepared by reacting four chloromethylaryl sulfones with 5-nitroimidazole derivatives via a vicarious nucleophilic substitution (VNS) of hydrogen reaction. Copyright Taylor & Francis Group, LLC.
Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore
Crozet, Maxime D.,Botta, Celine,Gasquet, Monique,Curti, Christophe,Remusat, Vincent,Hutter, Sebastien,Chapelle, Olivier,Azas, Nadine,De Meo, Michel,Vanelle, Patrice
scheme or table, p. 653 - 659 (2009/09/08)
To improve the antiparasitic pharmacophore, 20 5-nitroimidazoles bearing an arylsulfonylmethyl group were prepared from commercial imidazoles. The antiparasitic activity of these molecules was assessed against Trichomonas vaginalis, the in vitro cytotoxicity was evaluated on human monocytes and the mutagenicity was determined by the Salmonella mutagenicity assay. All IC50 on T. vaginalis were below the one of metronidazole. The determination of the specificity indexes (SIs), defined as the ratios of the cytotoxic activity and the antitrichomonas activity, indicated that 11 derivatives had a SI over the one of metronidazole. Molecules, bearing an additional methyl group on the 2-position, showed a lower mutagenicity than metronidazole. Moreover, three derivatives were characterized by a low mutagenicity and an efficient antitrichomonas activity.
Reactions of nitroheteroarenes with carbanions: Bridging aromatic, heteroaromatic and vinylic electrophilicity
Seeliger, Florian,Blazej, Sylwia,Bernhardt, Sebastian,Makosza, Mieczyslaw,Mayr, Herbert
experimental part, p. 6108 - 6118 (2009/07/18)
The relative rate constants for the vicarious nucleophilic substitution (VNS) of the anion of chloromethyl phenyl sulfone (1-) with a variety of nitroheteroarenes, for example, nitropyridines, nitropyrroles, nitroimidazoles, 2-nitrothiophene, and 4-nitropyrazole, have been determined by competition experiments. It was shown that nitropyridines are approximately four orders of magnitude more reactive than nitrobenzene. Among the five-membered heterocycles 2-nitrothiophene is the most active followed by nitroimidazoles and 4-nitropyrazole. Nitropyrroles are the least electrophilic nitroheteroarenes with reactivities comparable to nitrobenzene. Quantum chemically calculated methyl anion affinities (B3LYP/6-311 G(d,p)//B3LYP/ 6-31G(d)) of the nitroarenes correlated only moderately with the partial relative rate constants. The correlation of these activities with the LUMO energies of nitroarenes is even worse. By measuring the second-order rate constants of the addition of 1" to nitroarenes and to diethyl arylidenemalonates 10, it was possible to link the electrophilic reactivities of nitroheteroarenes with the comprehensive electrophilicity scale based on the linear-free-energyrelationship log k(20°C) = s(N + E).
A new synthetic approach for novel 4-substituted-5-nitroimidazoles
Crozet, Maxime D.,Perfetti, Patricia,Kaafarani, Mustapha,Vanelle, Patrice,Crozet, Michel P.
, p. 4127 - 4129 (2007/10/03)
A new synthetic approach, involving an SRN1 reaction of the anion of 1-methyl-4-phenylsulfonyl-methyl-5-nitro-1H-imidazole with 2,2-dinitropropane and a radical anion or a concerted radical reductive elimination of sulfonyl and nitro groups affords an original 5-nitroimidazole bearing a trisubstituted ethylenic double bond at 4-position.
Vicarious Nucleophilic Substitution of Hydrogen in Imidazole Derivatives
Makosza, Mieczyslaw,Kwast, Ewa
, p. 287 - 292 (2007/10/02)
Nitroderivatives of imidazole react with carbanions containing leaving groups at the carbanion center yielding products of vicarious nucleophilic substitution of hydrogen at positions activated by the nitro group.Some aspects of the orientation pattern ar
