65917-57-9Relevant academic research and scientific papers
Nitroimidazoles: Part VIII - 2-Amino-1-methyl-5-nitroimidazoles and Derivatives
Sudarsanam, V.,Nagarajan, K.,Arya, V. P.,Kaulgud, A. P.,Shenoy, S. J.,Shah, R. K.
, p. 989 - 996 (2007/10/02)
Treatment of 1-methyl-2-methylsulphonyl-5-nitroimidazole (3) with liquid ammonia gives 2-amino-1-methyl-5-nitroimidazole (2).With sodamide and 3, the major product is the sulphone (4). 2 is transformed by isocyanates into ureas (5a-c), while with 2-chloroethyl isocyanate, imidazolidinone (6) and aminooxazolinone (7) are obtained. 2 is less reactive towards isothiocyanates and gives under forcing conditions, thioureas (8a,b) and guanidines (9a,b).Amides (10a-c) are obtained from 2 by acylation and 10d-g from sulphone (3) by displacement reactions as also sulphamides (11a-c).Cyclic anhydrides and 2 lead to imides (13-15). 2 is transformed into schiff bases (16a-k), some of them being reduced by sodium borohydride to arylalkylamines (17a-c).The ethoxymethylene derivative (18) of 2 is transformed into a large number of formamidines (19a-r), (20a-c) and 21, some of them being further converted into the dichloroacetyl derivatives (22a-c).Reaction of 18 with sodium borohydride affords the ethoxymethylamine (23b) and methylamine derivative (23a).The latter is available from 2 along with dimethylamine by alkylation with methyl iodide.A less satisfactory route for 23a and 23c is displacement of sulphone group from 3 by appropriate amine.Analogous displacements on 3 provide the derivatives 23d,e and 24.The product from the reaction of 3 with sodium azide is the azido derivative (25).The aziridine (27) undergoes iodide-catalysed ring opening to form 29a and does not rearrange to the imidazoline (28).The aminoethanol derivative (29b) results from 27 by an acid-catalysed reaction.
Chemotherapeutically active nitro compounds, 4, 5-nitroimidazoles (part I)
Winkelmann,Raether,Gebert,Sinharay
, p. 2251 - 2263 (2007/10/05)
More than 135 new 2-methyl-5-nitroimidazoles substituted in 1-position and 1-methyl-5-nitroimidazoles substituted in 2-position were investigated for their activity against various protozoan species, in particular Entamoeba histolytica in the golden hamster, Trichomonas fetus, Trypanosoma brucei and T. cruzi in the NMRI mouse. Among the nitroimidazoles substituted in the 1-position only two preparations exhibited a similar effect as metronidazole against T. fetus. In the class of the nitroimidazoles substituted in the 2-position 16 compounds were as effective as metronidazole, 19 showed an effect superior to metronidazole, 1 was as good as tinidazole and 2 exhibited an activity superior to tinidazole against T. fetus. Only few compounds displayed any amoebicidal activity. Of the mono and bis-hydrazones of 1-methyl-5-nitroimidazole-2-aldehyde substituted in the 2-position 3 compounds had an amoebicidal effect 2 to 8 times stronger than that of metronidazole. Only few representatives of the 1-methyl-5-nitroimidazoles substituted in the 2-position produced a useful trypanocidal effect when given in relatively high doses. The structure-activity relationship of 5-nitroimidazole derivatives has been discussed.
