60666-28-6

Usage

Uses

Used in Medicinal Chemistry:
1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole is used as a building block for the development of new pharmaceutical compounds due to its potential reactivity and the presence of functional groups that can be further modified or utilized in the synthesis of bioactive molecules. 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole's structure may be particularly useful in the design of drugs targeting various diseases, including antimicrobial, antiparasitic, and anticancer applications.
Used in Organic Synthesis:
1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole is used as a synthetic intermediate for the preparation of other complex organic molecules. Its azidoethyl group suggests that it may be employed in click chemistry reactions, which are a powerful tool for the rapid and efficient assembly of molecular structures. The nitro group also makes it potentially useful in various organic synthesis pathways, allowing for the creation of a wide range of chemical products.
Used in Academic Research:
1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole is used as a research tool in the study of imidazole chemistry and its potential applications. Researchers may utilize 1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole to explore new reaction pathways, investigate the properties of imidazole derivatives, and develop novel synthetic strategies for the preparation of complex molecules.
Used in Industrial Processes:
1-(2-azidoethyl)-2-Methyl-5-nitro-1H-iMidazole may be employed in the chemical industry as a versatile building block for the production of various chemical products. Its reactivity and the presence of functional groups make it a valuable component in the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

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

• 30746-54-4 2-(5-nitro-2-methyl-1-imidazolyl)ethyl methanesulfonate 
• 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 

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 
• 55881-33-9 1-(2-aminoethyl)-2-methyl-5-nitro imidazole 

Relevant academic research and scientific papers

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.

Crystal Habit Modification of Metronidazole by Supramolecular Gels with Complementary Functionality

A series of bis(urea) compounds with complementary functional groups similar to the pharmaceutical drug metronidazole and a structural isomer isometronidazole have been synthesized. The gelation properties of these compounds were studied in various solvent/solvent mixtures. The mechanical strength of the isomeric gelators was compared using rheology, and the morphologies of the xerogels were analyzed by scanning electron microscopy. These gels were used as media for metronidazole crystallization resulting in a marked habit modification of the metronidazole crystals in the drug-mimicking gels. However, crystallization in the nonmimetic isomeric gel resulted in morphologies similar to the solution state. These results indicate that the drug-mimetic gels interact with the surface of the drug crystal giving rise to new morphologies.

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

Synthesis and biological activity of new metronidazole derivatives

The development of new antimicrobial and antiparasitic agents offers the possibility of generating structures of increased potency. To this end, three sulphonate ester derivatives of metronidazole were synthesized. Treatment of the tosylate analogue with NaSPh and NaN3 gave the thiophenolate and azide derivatives, respectively. Oxidation of phenylthio derivative with mCPBA afforded the sulfonyl analogue. Similarly, cycloaddition of azido-metronidazole with various symmetric acetylene compounds furnished the 1,2,3-triazole analogues. Treatment of dimethyl dicarboxylate metronidazole derivative with guanidine hydrochloride in the presence of base resulted in the formation of the ring-expanded (fat) derivative, triazolo-diazepam derivative of metronidazole. Treatment of chlorometronidazole with silylated quinolones gave the quinolone analogues of metronidazole. The antigardiasis and antifungal activities of the synthesized compounds were investigated. In addition, all synthesized compounds were evaluated for their in vitro anti-HIV activity in MT-4 cells as non-nucleoside reverse transcriptase inhibitors.

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.

Metronidazole-triazole conjugates: Activity against Clostridium difficile and parasites

Abstract Metronidazole has been used clinically for over 50 years as an antiparasitic and broad-spectrum antibacterial agent effective against anaerobic bacteria. However resistance to metronidazole in parasites and bacteria has been reported, and improved second-generation metronidazole analogues are needed. The copper catalysed Huigsen azide-alkyne 1,3-dipolar cycloaddition offers a way to efficiently assemble new libraries of metronidazole analogues. Several new metronidazole-triazole conjugates (Mtz-triazoles) have been identified with excellent broad spectrum antimicrobial and antiparasitic activity targeting Clostridium difficile, Entamoeba histolytica and Giardia lamblia. Cross resistance to metronidazole was observed against stable metronidazole resistant C. difficile and G. lamblia strains. However for the most potent Mtz-triazoles, the activity remained in a therapeutically relevant window.

EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS

Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.

Synthesis and antibacterial activity evaluation of metronidazole-triazole conjugates

Synthesis and antibacterial activity of metronidazole-triazole conjugates are reported. Total 21 hybrid compounds have been synthesized with different substitution pattern on the triazole ring in order to study their influence on the antibacterial activit

Hypoxia-Selective Antitumor Agents. 10. Bis(nitroimidazoles) and Related Bis(nitroheterocycles): Development of Derivatives with Higher Rates of Metabolic Activation under Hypoxia and Improved Aqueous Solubility

A series of analogues of the prviously described compound N--4-(2-nitroimidazol-1H-yl)butanamide (4), a novel hypoxic cell cytotoxin and radiosensitizer, have been prepared and evaluated for hypoxia-selective cytot

Hypoxia-selective antitumor agents. 8. Bis(nitroimidazolyl)alkanecarboxamides: A new class of hypoxia-selective cytotoxins and hypoxic cell radiosensitisers

A series of novel bis(nitroimidazolyl)alkanecarboxamides has been prepared and evaluated for hypoxia-selective cytotoxicity and hypoxic cell radiosensitisation in vitro and in vivo. The compounds were prepared by direct coupling of preformed side chain acid and amine components, using diethyl phosphorocyanidate at room temperature. Although designed to be bis- bioreductive prodrugs of DNA cross-linking agents, none of the compounds showed evidence of DNA cross-linking activity, being equally potent against cell lines deficient and proficient in repair of cross-links. However, one of these compounds, N-[2-(2-methyl-5-nitro-1H-imidazolyl)ethyl]-4-(2-nitro-1H- imidazolyl)butanamide (10; SN 24699), showed high hypoxic selectivity as a cytotoxin (rising to 200-fold after exposure to the drug for several hours) in the repair-proficient Chinese hamster cell line AA8. This selectivity was greater than observed for the alkylating 2-nitroimidazole (4; RB 6145) (40- fold) or simple mononitroimidazoles (5-25-fold). Investigation of structure- activity relationships for hypoxic selectivity of bis(nitroimidzoles) was restricted by their low aqueous solubility, but a certain minimum separation of the two nitroimidazole units (by more than five atoms) appears desirable. All the compounds radiosensitized hypoxic cells in vitro but were little more potent as radiosensitizers than the corresponding monomeric nitroimidazoles. Compound 10 caused additional cell killing in the KHT tumor when multiple drug doses were administered in combination with a single dose of radiation. It is not yet clear whether this activity reflects hypoxic cell radiosensitization or cytotoxicity toward hypoxic cells, but this new class of bis-bioreductive agent clearly warrants further investigation.