Nitroimidazoles was written by Cosar, Charles;Crisan, Cornel;Horclois, Raymond;Jacob, Robert M.;Robert, Jacques;Tchelitcheff, Serge;Vaupre, Roger. And the article was included in Arzneimittel-Forschung in 1966.Application of 3034-41-1 This article mentions the following:
2-Alkyl 2-(4 or 5)nitroimidazoles were synthesized. Thus, 380 g. 2-methylimidazole was dissolved in 926 ml. 10N H2SO4, to obtain 2-methylimidazole acid sulfate (red oil) which was nitrated by treating with 550 ml. HNO3 (d. 1.38) and then 160 ml. HNO3 (d. 1.49) and 640 ml. H2SO4 (d. 1.83) with cooling at 18° to give 39% 2-methyl-4(5)-nitroimidazole (I, R = Me), m. 255°. Similarly were prepared the following I (R, m.p., and % yield given): H, 306° (2.5N HCl), 64; Et, 158° (H2O), 29; iso-Pr, 180° (H2O), 31. II were prepared from I by alternate methods. Method A: 38.1 g. I (R = Me) was mixed with 25.2 g. EtOK (18% in EtOH) and 100 ml. HCONMe2, EtOH was distilled, the residue was diluted with 200 ml. HCONMe2 and 37.8 g. Me2SO4 added dropwise, and the mixture heated 3 hrs. at 100° to give 62% 1,2-dimethyl-4-nitroimidazole, m. 183° (iso-PrOH). Method B: 13 g. Et2SO4 was added dropwise to a mixture of 17 g. 4-nitroimidazole, 90 ml. 2.5N NaOH, and heated 20 min. at 45°; after cooling a new addition of 90 ml. NaOH and 13 g. Et2SO4 was made, and the mixture heated 45 min. at 45°. Extraction with CHCl3 gave 27% 5.8 g. 1-ethyl-4-nitroimidazole, m. 40°. Method C: By heating 2 hrs. at 140-5° a mixture of 12.7 g. I and 22.6 g. PhCH2Cl, there was obtained 57% 1-benzyl-2-methyl-4-nitroimidazole, m. 106°. Similarly were prepared the II in the first table. [TABLE OMITTED] 2-Methyl-5-nitroimidazole (635 g.) and 3.22 kg. HO-CH2CH2Cl was refluxed 24 hrs. to yield 41% 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, m. 160°. Similarly were prepared the III in the 2nd table. Esters of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole (IV) were prepared by reaction of acid chloride and C5H5N with the IV (R = H). Thus were prepared the following IV (R, m.p., and % yield given): Ac, 74°, 60; COCHCl2 87°, 51; COCMe3, 39°, 26; palmitoyl, 55°, 68; stearoyl, 51°, 34; CO-(CH2)2CO2H, 109°, 89; neutral succinate, 129°, 39; COCH:CHPh, 100°, 44; Bz, 102°, 89; COC6H4Cl-o, 104°, 61; COC6H4-OH-o, 154°, 15; COC6H4OMe-p, 102°, 56; COC6H2(OMe)3-3,4,5, 116°, 45; COC6H4NO2-p, 166°, 22; neutral phthalate, 130°, 13. Derivatives of 2-nitroimidazole were prepared: 1-methyl-2-nitroimidazole, m. 105°, and 1-(2-hydroxyethyl)-2-nitroimidazole, m. 116°. The NO2 in position 4 or 5 was studied by ir spectroscopy. The influence of the position of the nitro group and the nature of the other substituents on the antitrichomonas activity was studied. The 5-nitro derivatives were always found to be more active than derivatives of 4-nitroimidazole. In the 5-nitroimidazole series, the best products are those carrying a Me group in the 2-position and in the 1-position; a short saturated aliphatic chain being optionally substituted, and the presence of a hydroxy group decreasing considerably the toxicity of the product. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Application of 3034-41-1).
1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Application of 3034-41-1
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem