76529-47-0Relevant academic research and scientific papers
Potential radiosensitizing agents. 7. 4(5)-Iodo-5(4)-nitroimidazole derivatives
Gupta,Larroquette,Agrawal,Grodkowski,Neta
, p. 987 - 991 (2007/10/02)
A series of 4(5)-iodo-5(4)-nitro-1-substituted-imidazoles has been synthesized and tested for their ability to selectively radiosensitize hypoxic Chinese hamster cells (V-79) to the lethal effect of radiation. The reaction of 4(5)-iodo-5(4)-nitroimidazole with 1,2-epoxy-3-methoxypropane and ethyl α-chloroacetate produced two isomeric products in each case, which were identified by their NMR spectra. The ethyl esters were further reacted with 3-picolylamine to produce corresponding amides. The 5-iodo-4-nitroimidazole-1-N-(3-picolyl)acetamide on further reaction with m-chloroperbenzoic acid produced the corresponding N-oxide. These compounds were generally more toxic to V-79 cells than the 2-nitroimidazole derivatives and were found to be more effective radiosensitizers in vitro. The 5-iodo-4-nitroimidazole derivatives were more efficient as sensitizers than the 4-iodo-5-nitroimidazole derivatives, and the sensitizing efficiency of this class of agents was found to have significant correlation with their partition coefficients.
Nitroimidazoles: Part XI - Some Halonitro- and Dinitroimidazoles
Sudarsanam, V.,Nagarajan, K.,George, T.,Shenoy, S. J.,Iyer, V. V.,Kaulgud, A. P.
, p. 1022 - 1026 (2007/10/02)
Methylation of 2-chloro-4-nitroimidazole (6), obtained from imidazole in four steps, either with dimethyl sulphate or with diazomethane affords a mixture of 2-chloro-1-methyl-5-nitroimidazole (10) and the 4-nitro-isomer (7).The corresponding dinitro compounds 11 and 8 are formed in the methylation of 2,4-dinitroimidazole (5), 8 being converted to 7 by the action of POCl3.Reaction of 10 with the sodium salt of N-methanesulphonyl-2-imidazolidinone provides the potent amoebicide, 1-methylsulphonyl-3-(1-methyl-5-nitroimidazol-2-yl)-2-imidazolidinone (2).The isomer 14 issynthesised from 7 in low yield.Ethylation of 5 leads to preponderant N-alkylation, providing a mixture of 1-ethyl dinitroimidazoles (9) and (12), but a small amount of N,C-diethyl derivative 15 is also obtained.The formation of 15 from 5 is rationalised.The diiodination product of imidazole is shown to be 4,5-diiodoimidazole (19), nitric acid transforming it to 4-iodo-5-nitroimidazole (20).Methylation of 20 affords a mixture of isomeric 1-methyliodonitro derivatives (21) and (22).The structures of 21 and 22 are established by 13C NMR data as well as by conversion into morpholine derivatives 26 and 24 respectively which also arise from 1-methylchloronitroimidazoles (25) and (23).A mechanism is proposed for the reported conversion of 5 into 4-chloro-5-nitroimidazole (32) in boiling 2-chloroethanol.
