5213-48-9Relevant academic research and scientific papers
Carbanion Stabilization in C,N-Dimethylnitroimidazoles
Rav-Acha, C.,Cohen, Louis A.
, p. 4717 - 4720 (1981)
Kinetics of base-catalyzed exchange of C-methyl protons have been investigated for the six position isomers of C,N-dimethylnitroimidazoles (at 60 deg C in D2O-CD3OD, 1:1).Rates of exchange were based on the decrease in 1H NMR signals relative to those for the nonexchanging N-methyl groups.Values of kOD covered a range of 5*104; in 0.01 N NaOD, values of t1/2 range from 2.8 s to 38 h.The greatest kinetic acidity was found in 1,5-dimethyl-4-nitroimidazole and the least in 1,2-dimethyl-4-nitro- and 1,4-dimethyl-2-nitroimidazole.In the latter two compounds, the methyl and nitro groups have a "meta" relationship, their resistance to exchange indicates weak resonance stabilization of the respective carbanions.The value of kOD for 1,5-dimethyl-4-nitroimidazole (1485 M-1 min-1) is 4.8*106 as great as that for o-nitrotoluene but only 27-fold less than that for nitromethane.The result suggests that there may be significant localization in the 4,5-double bond of N-substituted imidazoles.The order of kinetic acidities for the C-methyl groups is consistent with the order of reactivities of the same compounds in aldol condensations.
Cellular pharmacology of evofosfamide (TH-302): A critical re-evaluation of its bystander effects
Hong, Cho Rong,Dickson, Benjamin D.,Jaiswal, Jagdish K.,Pruijn, Frederik B.,Hunter, Francis W.,Hay, Michael P.,Hicks, Kevin O.,Wilson, William R.
, p. 265 - 280 (2018)
Evofosfamide (TH-302) is a clinical-stage hypoxia-activated prodrug with proven efficacy against hypoxic cells in preclinical tumour models. TH-302 is designed to release the DNA crosslinking agent bromo-isophosphoramide mustard (Br-IPM) when reduced in h
Combating bacteria with nitroimidazolyl-triazolo-pyridiazine compounds
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, (2008/06/13)
Nitroimidazolyl-s-triazolo[4,3-b]pyridazines of the formula: SPC1 Wherein R is hydrogen or lower alkyl optionally substituted in the 2-position by hydroxyl or by lower acyloxy or lower alkoxy; A is hydrogen, halogen, azido, cyano; lower alkyl, alkoxy, alkylthio, alkylsulfonyl, carboxyl; lower alkoxycarbonyl, lower alkoxycarbonimidoyl; or hydrazino, carbamoyl, amidino or a carboximidohydrazide group optionally substituted by one or two lower acyl, alkyl or cycloalkyl radicals; or A is a radical of the formula: EQU1 wherein R1 and R2 are, individually, hydrogen or a number of organic radicals or, taken together, can be an alkylene bridge; and R3 is hydrogen or lower alkyl; or, together with R2, R3 can form an alkylene bridge; n is 0 or 1; And the pharmaceutically compatible thereof, possess high in vivo effectiveness as antimicrobials.
