22813-32-7

Basic information

• Product Name: 2-(2-NitroiMidazol-1-yl)acetic acid
• Synonyms: 2-(2-NitroiMidazol-1-yl)acetic acid;2-(2-Nitro-1H-imidazol-1-yl)acetic acid
• CAS NO: 22813-32-7
• Molecular Formula: C₅H₅N₃O₄
• Molecular Weight: 171.1109
• Mol File: 22813-32-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 487.2°Cat760mmHg
• Flash Point: 248.5°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 2.63E-10mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(2-NitroiMidazol-1-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-NitroiMidazol-1-yl)acetic acid(22813-32-7)
• EPA Substance Registry System: 2-(2-NitroiMidazol-1-yl)acetic acid(22813-32-7)

Safety Data

• Hazardous Substances Data: 22813-32-7(Hazardous Substances Data)

Usage

General Description

2-(2-NitroiMidazol-1-yl)acetic acid is a chemical compound that falls into the category of organic substances, specifically a derivative of imidazole. Imidazole derivatives are often used in a variety of applications in pharmaceuticals, as they can possess antimicrobial, antifungal, and antitumor properties. The exact properties and potential applications of 2-(2-NitroiMidazol-1-yl)acetic acid can vary, but it is likely to be characterized by similar qualities. Additionally, like other organic compounds, its structure is likely defined by the presence of carbon atoms, and its actions within a biological system would be dictated by its interactions with proteins and other cellular molecules.

InChI:InChI=1/C5H5N3O4/c9-4(10)3-7-2-1-6-5(7)8(11)12/h1-2H,3H2,(H,9,10)

Upstream product

• 22668-01-5 etanidazole 
• 127894-74-0 tert-butyl 2-(2-nitro-1H-imidazol-1-yl)acetate 
• 22813-31-6 methyl 2-(2-nitro-1H-imidazole-1-yl)acetate 
• 5006-67-7 2-(2-nitro-1H-imidazol-1-yl)-ethanol 

Downstream Products

• 199734-70-8 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl)acetate 
• 1383370-94-2 2-(2-nitro-imidazol-1-yl)-N-(4-sulfamoylphenyl)acetamide 
• 1383370-96-4 2-(2-nitro-imidazol-1-yl)-N-[2-(4-sulfamoylphenyl)ethyl]-acetamide 
• 1383370-95-3 2-(2-nitro-imidazol-1-yl)-N-(4-sulfamoylbenzyl)acetamide 
• 199800-19-6 FETA 
• 154094-89-0 N-[2-(2-methyl-5-nitro-1H-imidazolyl)ethyl]-2-(2-nitro-1H-imidazolyl)ethanamide 
• 131339-74-7 1-(t-butoxycarbonyl)-4-(2-nitroimidazol-1-ylacetyl)piperazine 

Relevant articles and documents

Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles

Reaction of Etanidazole (a 2-nitroimidazole derivative with an amide side-chain containing a hydroxyethyl group) with triflic anhydride gives, depending on conditions, a trifluoromethyl(sulfonyl)oxazolidine via a cyclization reaction, or a fluorine-free formate derivative; reaction with tosyl chloride gives only a chloroethyl derivative. An attempt to replace a Br-atom in a related propyl-containing amide side-chain by a F-atom forms instead a propylene derivative via loss of HBr. The studies stem from interest in use of 2-nitroimidazoles with fluorine-containing amide side-chains as hypoxia markers.

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.

Synthesis of new 18F-radiolabeled silicon-based nitroimidazole compounds

The syntheses of new nitroimidazole compounds using silicon-[ 18F]fluorine chemistry for the potential detection of tumor hypoxia are described. [18F]silicon-based compounds were synthesized by coupling 2-nitroimidazole with silyldinaphtyl or silylphenyldi-tert-butyl groups and labeled by fluorolysis or isotopic exchange. Dinaphtyl compounds (6, 10) were labeled in 56-71% yield with a specific activity of 45 GBq/μmol, however these compounds ([18F]7 and [18F]11) were not stable in plasma. Phenyldi-tert-butyl compounds were labeled in 70% yield with a specific activity of 3 GBq/μmol by isotopic exchange, or in 81% yield by fluorolysis of siloxanes with a specific activity of 45 GBq/μmol. The labeled compound [18F]18 was stable in plasma and excreted by the liver and kidneys in vivo. In conclusion, the fluorosilylphenyldi-tert-butyl (SiFA) group is more stable in plasma than fluorosilyldiphenyl moiety. Thus, compound [ 18F]18 is suitable for further in vivo assessments.