1010-93-1

Basic information

• Product Name: 2-methyl-5-nitroimidazol-1-ylacetic acid
• Synonyms: 2-Methyl-5-nitro-1H-imidazole-1-acetic acid;1H-Imidazole-1-acetic acid, 2-methyl-5-nitro-;Ccris 2147;Metronidazole IMpurity G;1-Carboxymethylmetronidazole;2-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetic acid;2-Methyl-5-nitroimidazole-1-acetic acid;Metronidazole-1-acetic acid
• CAS NO: 1010-93-1
• Molecular Formula: C₆H₇N₃O₄
• Molecular Weight: 185.14
• Mol File: 1010-93-1.mol

Chemical Properties

• Melting Point: 176-178 °C
• Boiling Point: 475.9°Cat760mmHg
• Flash Point: 241.6°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 7.28E-10mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 3.65±0.10(Predicted)
• Stability: Hygroscopic
• BRN: 613770
• CAS DataBase Reference: 2-methyl-5-nitroimidazol-1-ylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-5-nitroimidazol-1-ylacetic acid(1010-93-1)
• EPA Substance Registry System: 2-methyl-5-nitroimidazol-1-ylacetic acid(1010-93-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 1010-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-Methyl-5-nitroimidazol-1-ylacetic acid is used as a research compound for studying its mutagenic properties and potential effects on genetic material. Understanding its impact on DNA can contribute to the development of new drugs and therapies, as well as inform the safety profile of related compounds.
Used in Antimicrobial Studies:
As a metabolite of metronidazole, 2-methyl-5-nitroimidazol-1-ylacetic acid may be used in antimicrobial research to explore its potential as an active agent against various pathogens. This could lead to the discovery of new treatments for bacterial and parasitic infections.
Used in Toxicology and Safety Assessments:
The mutagenic activity of 2-methyl-5-nitroimidazol-1-ylacetic acid makes it a relevant compound for toxicology studies. It can be used to assess the potential risks and side effects associated with the use of metronidazole and other related drugs, helping to ensure the safety of these medications for patients.

InChI:InChI=1/C6H7N3O4/c1-4-7-2-5(9(12)13)8(4)3-6(10)11/h2H,3H2,1H3,(H,10,11)

Upstream product

• 443-48-1 metronidazole 
• 1016-40-6 ethyl 2-(2-methyl-5-nitro-1H-imidazole-1-yl)acetate 
• 56910-52-2 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetaldehyde 

Downstream Products

• 1016-40-6 ethyl 2-(2-methyl-5-nitro-1H-imidazole-1-yl)acetate 
• 1214889-81-2 N-[3-(3-fluoro-4-{4-[2-(2-methyl-5-nitro-imidazol-1-yl)-acetyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide 
• 1321532-26-6 methyl 2-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamido)-3-phenylpropanoate 
• 1321532-24-4 ethyl 2-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamido)-3-phenylpropanoate 
• 1321532-28-8 methyl 3-(4-hydroxyphenyl)-2-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamido)propanoate 
• 1342253-85-3 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-tosylacetamide 
• 1342253-86-4 N-(4-fluorophenylsulfonyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamide 
• 1342253-88-6 N-(4-bromophenylsulfonyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamide 
• 1342253-87-5 N-(4-chlorophenylsulfonyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamide 

Relevant articles and documents

Design and synthesis of vandetanib derivatives containing nitroimidazole groups as tyrosine kinase inhibitors in normoxia and hypoxia

Sixteen novel epidermal growth factor receptor (EGFR)/vascular endothelial growth factor (VEGF)-2 inhibitors (nitroimidazole-substituted 4-anilinoquinazoline derivatives (16a-p)) were designed and prepared via the introduction of a nitroimidazole group in the piperidine side chain and modification on the aniline moiety of vandetanib. Preliminary biological tests showed that comparing with vandetanib, some target compounds exhibited excellent EGFR inhibitory activities and anti-proliferative over A549/H446 cells in hypoxia. Meanwhile, several of the above compounds demonstrated better bioactivity than vandetanib in VEGF gene expression inhibition. Owing to the excellent IC50 value (1.64 μmol/L), the inhibition ratios of 16f over A549 and H446 cells were 62.01% and 59.86% at the concentration of 0.5 μM in hypoxia, respectively. All of these results indicated that 16f was a potential cancer therapeutic agent in hypoxia and was worthy of further development.

Preparation and biological evaluation of metronidazole derivatives with monoterpenes and eugenol

Two series of metronidazole derivatives (ester derivatives and ether derivatives) were prepared reacting metronidazole and its acetic acid oxidized form with menthol, thymol, carvacrol, and eugenol. Both series of compounds were tested in vitro against tw

A by the MTZ preparation of amine derivatives furan warm and its preparation and in antibacterial drugs in the application of the

The invention relates to a furanone aniline derivate prepared from metronidazole, as well as a preparation method and applicable of the furanone aniline derivate in antibacterial drugs. The derivant is named as 4-((3,5-dimethoxy phenyl) amino)-3-(2-methyl-5-nitro-1H-iminazol-1-radical)furan-2(5H)-ketone. The derivant represents a better inhibiting and killing effect on to-be-tested bacteria, the inhibiting activity of bacillus subtilis is close to that of positive control kanamycin, and the inhibiting activity of the staphylococcus epidermidis exceeds that of positive control kanamycin, so that the derivant can be used for preparing anti-infective drugs; the influence due to configuration interconversion is improved by replacing the acrylate part of a lead compound with a furan ketone ring, a metronidazole structure with stronger antimicrobial action is introduced, and on the basis of in-depth study of the structure-function relationship, a novel antibacterial derivate with a higher activity is designed and synthesized, and the preparation method of the derivate is provided.

Anilinoquinazoline compound containing nitroimidazole group and preparation method and application thereof

The invention provides a brand new anilinoquinazoline compound of the structure in the formula (I). The anilinoquinazoline compound has a tyrosine kinase inhibiting effect. Real-time fluorogenic quantitative PCR measurement results indicate that the VEGF

TREATMENTS FOR GASTROINTESTINAL CONDITIONS

Compounds for the treatment of bacterial and parasitic infections which are hybrid compounds of compounds having antibacterial or antiparasitic activity and compounds that decrease the absorption of the hybrid compound from the gastrointestinal tract. The compounds are preferably for use against C. difficile infections and comprise a hybrid molecule of an anti-C. difficile compound such as a nitroimidazole and a tetramic acid derivative.

COMPOUNDS AND METHODS FOR SELECTIVE IMAGING AND/OR ABLATION

The invention relates generally to compounds and methods for imaging and/or selective ablation of nitroreductase-expressing cells and/or biological agents. More particularly, although not exclusively, the invention provides compounds that are selectively metabolised by bacterial nitroreductases and are substantially insensitive to metabolism under oxic or hypoxic conditions by human nitroreductase enzymes.

Synthesis of new compounds derived from metronidazole and amino acids and their esters as antiparasitic agents

A number of new compounds derived from metronidazole and amino acids and their esters have been synthesized through a reaction between 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetic acid and a number of amino acid esters in the presence of N,N'carbonyldiimidazole (CDI). Hydrolysis of the esters derivatives with sodium hydroxide (4%) followed by acidification with hydrochloric acid (3 M) afforded the corresponding acids. The newly synthesized compounds were characterized by elemental analysis and by spectroscopic techniques such as 1H-NMR, 13C-NMR, and mass spectrometry. Some of the prepared compounds exhibited lethal activity against pathogenic protozoan parasites. Springer Science+Business Media, LLC 2011.

Metronidazole acid acyl sulfonamide: A novel class of anticancer agents and potential EGFR tyrosine kinase inhibitors

A series of novel metronidazole derivatives were recently reported as potent anticancer agents targeting EGFR and HER-2 by our group [Qian, Y.; Zhang, H. J.; Zhang, H.; Xu, C.; Zhao, J.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 4991]. Based on the previous

Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents

A series of N-alkylated derivatives of nitroimidazolyl oxazolidinones 6a-i with various substituent at N-1 position of the nitroimidazole were synthesized and their in-vitro antibacterial activities were evaluated against several Gram-positive and Gram-ne

Convenient syntheses of 5-[(2-Methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3, 4-oxadiazole-2(3H)thione and N-substituted 2-amino-5-[(2-methyl-5-nitro-1H- imidazol-1-yl)methyl]-1,3,4-thiadiazoles

(Chemical Equation Presented) Oxidation of metronidazole (4) with sodium dichromate yielded the corresponding 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetic acid (5) which was esterified with 1-butanol to give butyl 2-(2-methyl-5-nitro- 1H-imidazol-1-yl)acetate (8). Reaction of the latter with hydrazine hydrate gave 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide (9). Compound 5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione (10) could be obtained through the reaction of compound 9 with carbon disulfide in basic medium. Subsequent alkylation of compound 10 afforded alkyl 2-(5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio) acetate (11) in good yield. Reaction of hydrazide 9 with substituted isothiocynate yielded 1-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetyl]-4-aryl(or ethyl)thiosemicarbazide (12) which was cyclized in acidic media to N-substituted 2-amino-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-thiadiazole (13).