16156-90-4

Basic information

• Product Name: 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole
• Synonyms: 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole;1-(2-Iodoethyl)-2-methyl-5-nitro-1H-imidazole
• CAS NO: 16156-90-4
• Molecular Formula: C₆H₈IN₃O₂
• Molecular Weight: 281.05
• Mol File: 16156-90-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 395.1°Cat760mmHg
• Flash Point: 192.8°C
• Appearance: /
• Density: 2.03g/cm³
• Vapor Pressure: 4.29E-06mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole(16156-90-4)
• EPA Substance Registry System: 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole(16156-90-4)

Safety Data

• Hazardous Substances Data: 16156-90-4(Hazardous Substances Data)

Usage

General Description

1-(2-iodoethyl)-2-methyl-5-nitro-imidazole is a chemical compound that consists of an imidazole ring with a 2-iodoethyl group and a 2-methyl-5-nitro substituent. 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole is commonly used as a pharmaceutical intermediate in the synthesis of various medications, particularly antimicrobial and antifungal agents. It is also used in research and development as a building block for the creation of new drug candidates and chemical derivatives. Additionally, it has potential applications in the agricultural industry as a pesticide or herbicide. Overall, 1-(2-iodoethyl)-2-methyl-5-nitro-imidazole is a versatile and important chemical compound with various uses in pharmaceuticals, research, and agriculture.

InChI:InChI=1/C6H8IN3O2/c1-5-8-4-6(10(11)12)9(5)3-2-7/h4H,2-3H2,1H3

Upstream product

• 443-48-1 metronidazole 
• 13182-81-5 1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole 
• 30746-54-4 2-(5-nitro-2-methyl-1-imidazolyl)ethyl methanesulfonate 
• 6058-57-7 1-(2-bromoethyl)-2-methyl-5-nitroimidazole 

Relevant articles and documents

Synthesis and evaluation of a new 99mTc(I)-tricarbonyl complex bearing the 5-nitroimidazol-1-yl moiety as potential hypoxia imaging agent

The objective of this work was to develop a novel 99mTc complex bearing the 5-nitroimidazol-1-yl moiety with recognised selectivity towards hypoxic tissue, as a potential radiopharmaceutical for imaging tumour hypoxia.The new metronidazole derivative (2-amine-3-[2-(2-methyl-5-nitro-1H- imidazol-1-yl)ethylthio]propanoic acid) (L) containing adequate groups to coordinate technetium through the formation of a Tc(I)-tricarbonyl complex was synthesised with adequate yield (33%) and characterised by spectroscopy. Labelling was performed by substitution of three labile water molecules of the technetium tricarbonyl precursor, fac-[99mTc(CO)3(H 2O)3]+ with the ligand. A radiochemical purity higher than 90% was achieved and remained unchanged for more than 4 h. The complex has a high stability in plasma, a moderate plasma protein binding and a moderate hydrophilicity.In vitro cell uptake studies showed a ratio between the activity taken up by cells in hypoxia/normoxia of 1.6 ± 0.4 (p 0.5).Biodistribution in normal mice showed rapid depuration and low uptake in all organs and tissues except liver. Biodistribution in mice bearing induced tumours showed a low tumour uptake, but tumour/muscle ratio was favourable thanks to depuration. Comparison with biological results of other metronidazole derivatives clearly shows that modifications of the chelator are very important and contribute to improve the biological behaviour.

DUAL ACTION CARBONIC ANHYDRASE INHIBITORS

The present invention is directed to novel carbonic anhydrase IX inhibitors comprising a nitroimidazole moiety substituted with a heterocycle or phosphinate and having sulfonamide, sulfamate or sulfamide groups. The present invention is also related to the use of these novel carbonic anhydrase IX inhibitors in cancer treatment, especially radiotherapy and chemotherapy and the use in treatment of infections.

Synthesis and biological characterisation of novel dithiocarbamate containing 5-nitroimidazole 99mTc-complexes as potential agents for targeting hypoxia

With the aim to develop new potential 99mTc-radiopharmaceuticals for imaging hypoxia based on the formation of Tc-nitrido complexes, two novel dithiocarbamate containing metronidazole derivatives (L1 and L2) have been prepared and characterised. The synthesis of L1 and L2 was achieved in excellent yield and high purity. Labelling with 99mTc was successfully performed using a low ligand concentration (approximately 2-3 mg) and the desired products were obtained with high radiochemical purity (>90%). Lipophilicity, plasma protein binding, and biodistribution in normal- and tumour-bearing-CD1 mice studies were performed to asses the potentiality for nuclear medicine oncology. According to the physicochemical and biological behaviour both in healthy animals and in animals bearing solid tumours complex dtcTc1 could be considered as a starting point for the development of new radiopharmaceuticals for imaging hypoxia.