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Nitroimidazole

Nitroimidazole

Nitroimidazoles are the group of organic compounds consisting of an imidazole ring with at least one nitro group substituent. The term also refers to the class of antibiotics that have nitroimidazole in their structures. These antibiotics commonly include the 5-nitroimidazole positional isomer.

Synthesis

Imidazole undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid to give 5-nitroimidazole.

Nitroimidazole antibiotics

Position numbers on the ring

From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro functional group. Structures with names 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, pretomanid, ornidazole, megazol, and azanidazole. Drugs based on 2-nitroimidazoles include benznidazole and azomycin.

Nitroimidazole antibiotics have been used to combat anaerobic bacterial and parasitic infections. Perhaps the most common example is metronidazole. Other heterocycles such as nitrothiazoles (thiazole) are also used for this purpose. Nitroheterocycles are thought to be reductively activated in hypoxic cells, and then undergo chemical decomposition to form toxic radical products.

References

References

  1. [https://www.sigmaaldrich.com/US/en/product/aldrich/141615 4-Nitroimidazole] at [[Sigma-Aldrich]]
  2. (1993). "Nitroimidazole drugs-action and resistance mechanisms I. Mechanism of action". Journal of Antimicrobial Chemotherapy.
  3. Jenks, Peter J.. (2010-01-01). "CHAPTER 24 - Nitroimidazoles". W.B. Saunders.
  4. Mital A. (2009). "Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships". Sci Pharm.
  5. (1989). "Bioactivation in chemical teratogenesis". Annu. Rev. Pharmacol. Toxicol..
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