Nitroimidazole
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| Names | |
|---|---|
| IUPAC name
5-Nitro-1H-imidazole | |
| Identifiers | |
100214-79-7  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 10637918  |
| PubChem | 18208 |
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| Properties | |
| C3H3N3O2 | |
| Molar mass | 113.07 g/mol |
| Melting point | 303 °C (577 °F; 576 K) (decomposes) |
| Hazards | |
| Main hazards | Xn |
| R-phrases | R20/21/22 R36/37/38 |
| S-phrases | S26 S36/37 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
5-Nitroimidazole is an organic compound with the formula O2NC3H2N2H. The nitro group at position 5 on the imidazole ring is the most common positional isomer. The term nitroimidazole also refers to a class of antibiotics that share similar chemical structures.[2]
2-Nitroimidazole (azomycin) is used in the synthesis of Etanidazole.
Synthesis
Imidazole reacts with a mixture of nitric acid to give 5-nitroimidazole:
- C3H3N2H + HNO3 → O2NC3H2N2H + H2O
Under conventional conditions for nitration, the reaction is conducted in the presence of sulfuric acid.
Nitroimidazole antibiotics
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.
Nitroimidazole antibiotics have been used to combat anaerobic bacterial and parasitic infections.[3] Perhaps the most common example is metronidazole. 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
- ↑ 4-Nitroimidazole at Sigma-Aldrich
- ↑ Edwards, David I. "Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action" Journal of Antimicrobial Chemotherapy 1993, volume 31, pp. 9-20. doi:10.1093/jac/31.1.9.
- ↑ Mital A (2009). "Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships". Sci Pharm. 77 (3): 497–520. doi:10.3797/scipharm.0907-14.
- ↑ Juchau, MR (1989). "Bioactivation in chemical teratogenesis". Annu. Rev. Pharmacol. Toxicol. 29: 165–167. doi:10.1146/annurev.pa.29.040189.001121. PMID 2658769.