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5-Nitroimidazole is an organic compound with the formula O₂NC₃H₂N₂H. 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

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 and pimonidazole.

Nitroimidazole antibiotics have been used to combat anaerobic bacterial and parasitic infections.^[3] Perhaps the most common example is 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]

Three nitroimidazoles: metronidazole, tinidazole, and nimorazole

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.

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English Journal

Molecularly imprinted solid phase extraction method for simultaneous determination of seven nitroimidazoles from honey by HPLC-MS/MS.

Guo XC1, Xia ZY1, Wang HH2, Kang WY1, Lin LM3, Cao WQ3, Zhang HW3, Zhou WH4.
Talanta.Talanta.2017 May 1;166:101-108. doi: 10.1016/j.talanta.2017.01.047. Epub 2017 Jan 16.
In this work, a selective sample cleanup procedure that combined molecular imprinting technique with solid phase extraction was developed for the simultaneous extraction of the seven nitroimidazoles (NMZs) from honey samples. The molecular imprinting polymers for NMZs were prepared through bulk poly
PMID 28213209

Hydrothermal synthesis of polyethylenimine-protected high luminescent Pt-nanoclusters and their application to the detection of nitroimidazoles.

Xu N1, Li HW2, Wu Y3.
Analytica chimica acta.Anal Chim Acta.2017 Mar 15;958:51-58. doi: 10.1016/j.aca.2016.12.033. Epub 2016 Dec 28.
A novel one-step hydrothermal synthesis of highly fluorescent platinum nanoclusters protected by polyethylenimine (Pt-NCs@PEI) is described. The products are characterized well by UV-vis absorption, fluorescence spectra, X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TE
PMID 28110684

Myocarditis in different experimental models infected by Trypanosoma cruzi is correlated with the production of IgG1 isotype.

Caldas IS1, Diniz LF2, Guedes PM3, Nascimento ÁF4, Galvão LM5, Lima WG4, Caldas S6, Bahia MT4.
Acta tropica.Acta Trop.2017 Mar;167:40-49. doi: 10.1016/j.actatropica.2016.12.015. Epub 2016 Dec 16.
This study was designed to verify the relationship between IgG antibodies isotypes and myocarditis in Trypanosoma cruzi infection using mice and dogs infected with different T. cruzi strains. The animals were infected with benznidazole-susceptible Berenice-78 and benznidazole-resistant AAS and VL-10
PMID 27993495

Japanese Journal

Development of a Hypoxia-Selective Near-Infrared Fluorescent Probe for Non-invasive Tumor Imaging

Youssif Bahaa Gamal Mohamed,Okuda Kensuke,Kadonosono Tetsuya,Salem Ola Ibrahim Abdel Razek,Hayallah Alaa Arafat Mohamed,Hussein Mostafa Ahmed,Kizaka-Kondoh Shinae,Nagasawa Hideko
Chemical and Pharmaceutical Bulletin 60(3), 402-407, 2012
… Efficient synthesis was achieved by nucleophilic substitution and click chemistry ring using the bifunctional tetraethylene glycol linker 2 containing thiol and azide groups for the conjugation of the propargylated nitroimidazole 1 and the heptamethine cyanine dye 3 bearing a 2-chloro-1-cyclohexenyl ring. …
NAID 130001852429

KORTUCが開く新しい世界 : 歴史的経緯をふまえて (特集酵素標的・増感放射線療法KORTUCの基礎と臨床)

猪俣泰典,新保大樹,吉川信彦他
癌の臨床 57(6), 307-312, 2011-12-00
NAID 40019479527

Quantitative Structure Activity Relationship Modeling for Predicting Radiosensitization Effectiveness of Nitroimidazole Compounds

LONG Wei,LIU Peixun
Journal of radiation research 51(5), 563-572, 2010-09-16
… This paper provides quantitative structure activity relationship (QSAR) models for predicting the radiosensitization effectiveness of nitroimidazole compounds. … The provided models were useful tools to predict the radiosensitization effectiveness of nitroimidazole compounds. …
NAID 10026644392

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5-Nitroimidazole^[1]
Names
	IUPAC name 5-Nitro-1H-imidazole
Identifiers
CAS Number	100214-79-7
ChemSpider	10637918
Jmol interactive 3D	Image
PubChem	18208
	InChI InChI=1S/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H Key: KUNMIWQQOPACSS-UHFFFAOYSA-N ; InChI=1/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H Key: KUNMIWQQOPACSS-UHFFFAOYAV ;
	SMILES c1cn(cn1)[N+](=O)[O-] ;
Properties
Chemical formula	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