60666-28-6

Basic information

• Product Name: 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole
• Synonyms: 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole
• CAS NO: 60666-28-6
• Molecular Formula: C₆H₈N₆O₂
• Molecular Weight: 196.16672
• EINECS: -0
• Mol File: 60666-28-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole(60666-28-6)
• EPA Substance Registry System: 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole(60666-28-6)

Safety Data

• Hazardous Substances Data: 60666-28-6(Hazardous Substances Data)

Usage

General Description

1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole is a chemical compound that belongs to the class of imidazole derivatives. It contains a nitro group and a azidoethyl group, making it potentially reactive and useful in various chemical reactions. The presence of the azidoethyl group suggests that it may be used in click chemistry reactions, and the nitro group makes it potentially useful in organic synthesis. 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole may have potential applications in medicinal chemistry, as nitroimidazoles have been investigated for their antimicrobial, antiparasitic, and anticancer properties. Overall, the compound's structure suggests that it may have diverse applications in both academic research and industrial processes.

InChI:InChI=1/C6H8N6O2/c1-5-8-4-6(12(13)14)11(5)3-2-9-10-7/h4H,2-3H2,1H3

Upstream product

• 30575-42-9 toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester 
• 6058-57-7 1-(2-bromoethyl)-2-methyl-5-nitroimidazole 
• 28795-25-7 2-methyl-5-nitro-1-[2-(phenylsulfonyl)ethyl]-1H-imidazole 
• 54252-00-5 2-methyl-5-nitro-1-[2-(phenylthio)ethyl]-1H-imidazole 
• 443-48-1 metronidazole 
• 30746-54-4 2-(5-nitro-2-methyl-1-imidazolyl)ethyl methanesulfonate 

Downstream Products

• 1144040-20-9 1-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]-4-(o-tolyloxymethyl)-1H-[1,2,3]triazole 
• 1144040-19-6 1-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]-4-(phenoxymethyl)-1H-[1,2,3]triazole 
• 1144040-22-1 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-4-m-tolyloxymethyl-1H-[1,2,3]triazole 
• 1144040-21-0 1-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]-4-(p-tolyloxymethyl)-1H-[1,2,3]triazole 
• 1144040-28-7 4-(2-chloro-phenoxymethyl)-1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazole 
• 1144040-29-8 4-(4-chloro-phenoxymethyl)-1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazole 
• 1144040-27-6 1-(4-{1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazol-4-ylmethoxy}-phenyl)-ethanone 
• 1144040-23-2 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-4-(2-nitro-phenoxymethyl)-1H-[1,2,3]triazole 
• 1144040-24-3 1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-4-(4-nitro-phenoxymethyl)-1H-[1,2,3]triazole 
• 1144040-25-4 2-{1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazol-4-ylmethoxy}-benzaldehyde 
• 1144040-26-5 4-{1-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-1H-[1,2,3]triazol-4-ylmethoxy}-benzaldehyde 
• 1144040-35-6 1-(1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)cyclohexanol 
• 1144040-32-3 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-phenyl-1H-1,2,3-triazole 
• 1485819-27-9 C₁₈H₁₇N₇O₄ 

Relevant articles and documents

Influence of ligand denticity on the properties of novel 99mTc(I)-carbonyl complexes. Application to the development of radiopharmaceuticals for imaging hypoxic tissue

An important issue in the development of metal-based radiopharmaceuticals is the selection of the labelling strategy in order to couple the metal to the pharmacophore without losing the biological activity. With the aim to evaluate the correlation between ligand denticity and biological behaviour of the corresponding 99mTc complexes, we designed a tridentate and a bidentate 5-nitroimidazole derivatives suitable for 99mTc(I) tricarbonyl complexation and with potential use as radiopharmaceuticals towards hypoxic tissue diagnosis. Ligands were synthesized using metronidazol, a pharmaceutical containing the bioreductive pharmacophore as starting material. The chelating units were connected to the pharmacophore using the click reaction of Huisgen. Both 99mTc complexes were obtained in high yield and were hydrophilic and stable in labelling milieu. The complex obtained from the tridentate ligand exhibited high stability in human plasma, low protein binding and a favourable biodistribution characterized by low blood and liver uptake, fast elimination and negligible uptake in other organs or tissues. Selective uptake and retention in tumour together with favourable tumour/muscle ratio makes this 99mTc-complex a promising candidate for further evaluation as potential hypoxia imaging agent in tumours. The bidentate ligand, on the other hand, yielded a less stable 99mTc-complex that experimented hydrolysis in vitro and decomposition in human plasma and showed high protein binding, high blood and liver uptake and moderate excretion. Although selective uptake and retention in tumour was also observed physicochemical and biological behaviour are inadequate for in vivo use, demonstrating that denticity of the ligand is particularly important and that tridentate ligands are preferable in order to prepare 99mTc-tricarbonyl complexes for Nuclear Medicine imaging.

Synthesis, antiamoebic activity and docking studies of metronidazole-triazole-styryl hybrids

A series of 22 novel metronidazole-triazole-styryl hybrids were synthesized and evaluated for their in vitro antiamoebic activity against HM1: IMSS strain of Entamoeba histolytica. Some of the hybrids were found to be more active (IC50 = 0.12–0

Anti-methicillin resistant Staphylococcus aureus activity, synergism with oxacillin and molecular docking studies of metronidazole-triazole hybrids

MRSA causes 60-70% of Staphylococcus aureus infection in hospitals and it has developed resistance against the currently available drugs. Interestingly, a series of 35 metronidazole-triazole hybrids on screening against MRSA were found to be active. Compound 22 was found to be effective at 4 μg/mL concentration against nine strains of MRSA. The inhibitory activity was further enhanced upto 1 μg/mL when this compound was used in combination with oxacillin in 1:1 ratio. All the compounds were found to be non-toxic in THP-1 cell line upto a concentration of 50 μM. The time-kill kinetics studies suggested bacteriostatic nature of the compounds. In silico studies show that these compounds interact with Thr600, Ser598, Asn464, His583 and Tyr446 in the active site of PBP2a crystal structure from MRSA.