5-Nitroimidazole is an organic compound with the formula O 2NC 3H 2N 2H. It is the most common isomer of imidazole containing one nitro group. The term nitroimidazole also refers to a class of antibiotics that share similar chemical structures. [2 ]
Synthesis [ edit ]
Imidazole reacts with a mixture of nitric acid to give 5-nitroimidazole:
3H 3N 2H + HNO 3 → O 2NC 3H 2N 2H + H 2O
Under conventional conditions for
nitration, the reaction is conducted in the presence of sulfuric acid.
Nitroimidazole antibiotics [ edit ]
From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro
functional group. 4- and 5-nitroimidazole are equivalent from the perspective of drugs since these tautomers readily interconvert. Drugs of the 5-nitro variety include metronidazole, tinidazole, nimorazole, dimetridazole, 6-Amino PA824, ornidazole, megazol, and azanidazole. Drugs based on 2-nitromidazoles include benznidazole and pimonidazole.
Nitroimidazole antibiotics have been used to combat
anaerobic bacterial and parasitic infections. Perhaps the most common example is [3 ] metronidazole ( Flagyl). Other heterocycles such as nitrothiazoles ( thiazole) are also used for this purpose. Nitroheterocycles may be reductively activated in hypoxic cells, and then undergo redox recycling or decompose to toxic products. [4 ]
References [ edit ]