Nitroimidazole

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5-Nitroimidazole[1]
4-Nitroimidazole.svg
Names
Preferred IUPAC name
5-Nitro-1H-imidazole
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.296 Edit this at Wikidata
EC Number
  • 221-224-7
UNII
  • InChI=1S/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H checkY
    Key: KUNMIWQQOPACSS-UHFFFAOYSA-N checkY
  • c1cn(cn1)[N+](=O)[O-]
Properties
C3H3N3O2
Molar mass 113.076 g·mol−1
Melting point 303 °C (577 °F; 576 K) (decomposes)
Hazards
GHS pictograms GHS07: Exclamation mark
GHS Signal word Warning
H302
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Synthesis

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

C3H3N2H + HNO3 + H2SO4 → O2NC3H2N2H + H2O

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-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]

Three nitroimidazole antibiotics: metronidazole, tinidazole, and nimorazole

References

  1. ^ 4-Nitroimidazole at Sigma-Aldrich
  2. ^ Edwards, David I. (1993). "Nitroimidazole drugs-action and resistance mechanisms I. Mechanism of action". Journal of Antimicrobial Chemotherapy. 31 (1): 9–20. doi:10.1093/jac/31.1.9. PMID 8444678.
  3. ^ Mital A (2009). "Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships". Sci Pharm. 77 (3): 497–520. doi:10.3797/scipharm.0907-14.
  4. ^ Juchau, MR (1989). "Bioactivation in chemical teratogenesis". Annu. Rev. Pharmacol. Toxicol. 29: 165–167. doi:10.1146/annurev.pa.29.040189.001121. PMID 2658769.