30746-54-4

Usage

Uses

Used in Pharmaceutical Industry:
2-methyl-5-nitro-1H-imidazole-1-ethyl methanesulphonate is used as an antiprotozoal agent for the treatment of parasitic infections such as giardiasis and trichomoniasis. Its ability to disrupt the DNA synthesis of protozoa makes it effective against both standard and resistant strains of these parasites.
As a sulfonate compound, 2-methyl-5-nitro-1H-imidazole-1-ethyl methanesulphonate can be administered orally or topically, providing flexibility in treatment options and enhancing patient compliance. Its broad-spectrum activity against various protozoa and its effectiveness in resistant strains contribute to its value in the pharmaceutical industry for managing parasitic infections.

InChI:InChI=1/C7H11N3O5S/c1-6-8-5-7(10(11)12)9(6)3-4-15-16(2,13)14/h5H,3-4H2,1-2H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 443-48-1 metronidazole 

Downstream Products

• 60666-28-6 [2-(2-methyl-5-nitro-1H-imidazol-1-yl)]ethylazide 
• 1214753-00-0 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-(2-methoxyphenyl)piperazine-1-carbodithioate 
• 1214753-01-1 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-(4-nitrophenyl)piperazine-1-carbodithioate 
• 1239750-73-2 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-p-tolyl-acrylate 
• 1239750-82-3 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(2-fluorophenyl)acrylate 
• 1239750-83-4 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(2-chlorophenyl)acrylate 
• 1239750-92-5 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(3-fluorophenyl)acrylate 
• 1239750-68-5 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-chlorophenyl)acrylate 
• 1239750-85-6 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(2-bromophenyl)acrylate 
• 1239750-69-6 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-bromophenyl)acrylate 
• 1239750-74-3 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-methoxyphenyl)acrylate 
• 1239750-88-9 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(2-methoxyphenyl)acrylate 
• 1239750-93-6 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(3-methoxyphenyl)acrylate 
• 1239750-90-3 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(3-nitrophenyl)acrylate 

Relevant academic research and scientific papers

Design, synthesis, in vitro inhibition and toxicological evaluation of human carbonic anhydrases I, II and IX inhibitors in 5-nitroimidazole series

With the aim to obtain novel compounds possessing both strong affinity against human carbonic anhydrases and low toxicity, we synthesised novel thiourea and sulphonamide derivatives 3, 4 and 10, and studied their in vitro inhibitory properties against human CA I, CA II and CA IX. We also evaluated the toxicity of these compounds using zebrafish larvae. Among the three compounds, derivative 4 showed efficient inhibition against hCA II (KI = 58.6 nM). Compound 10 showed moderate inhibition against hCA II (KI = 199.2 nM) and hCA IX (KI = 147.3 nM), whereas it inhibited hCA I less weakly at micromolar concentrations (KI = 6428.4 nM). All other inhibition constants for these compounds were in the submicromolar range. The toxicity evaluation studies showed no adverse effects on the zebrafish larvae. Our study suggests that these compounds are suitable for further preclinical characterisation as potential inhibitors of hCA I, II and IX.

Synthesis and leishmanicidal evaluation of sulfanyl- and sulfonyl-tethered functionalized benzoate derivatives featuring a nitroimidazole moiety

A series of new nitroimidazole-containing derivatives was synthesized by coupling of 2-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylthio]ethanol with diversely substituted benzoic acids. Upon treatment with m-CPBA, 12 of these sulfanyl compounds were further oxidized to their sulfonyl analogs. All the 26 synthetic compounds were examined for in vitro activity against Leishmania (V.) braziliensis and Leishmania (L.) mexicana, and some of them displayed an efficient antileishmanial activity. Among the compounds tested, the catecholic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4-dihydroxybenzoate (9a, LC50 = 13 and 11 μM) and the pyrogallolic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4,5-trihydroxybenzoate (9b, LC50 = 4 and 1 μM) were the most active ones against the two Leishmania strains.

A rifamycin - nitro imidazole coupled molecular preparation method of (by machine translation)

The invention discloses a rifamycin - nitro imidazole coupling molecule of the preparation method. Preparation method of this invention to MTZ as raw materials, by changing the synthetic route, overcomes the reaction conditions must be controlled to the defect under the low temperature condition, and has improved the yield of target product. (by machine translation)

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.

NITROIMIDAZOLE COMPOUNDS AND THEIR USE IN CANCER THERAPY

The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof, formula (I) wherein m, n, X, Y and Z are as defined herein. Also provided are pharmaceutical compositions containing compounds of Formula (I), and methods of treating cancer and/or improving the response of tumors to radiotherapy by administering a compound of Formula (I) to a warm-blooded animal.

Novel nitroimidazole alkylsulfonamides as hypoxic cell radiosensitisers

A novel class of nitroimidazole alkylsulfonamides have been prepared and evaluated as hypoxia-selective cytotoxins and radiosensitisers. The sulfonamide side chain markedly influences the physicochemical properties of the analogues: lowering aqueous solubility and raising the electron affinity of the nitroimidazole group. The addition of hydroxyl or basic amine groups increased aqueous solubility, with charged amine groups contributing to increased electron affinity. The analogues covered the range of electron affinity for effective radiosensitisation with one-electron reduction potentials ranging from -503 to -342 mV. Cytotoxicity under normoxia or anoxia against a panel of human tumour cell lines was determined using a proliferation assay. 2-Nitroimidazole sulfonamides displayed significant hypoxia-selective cytotoxicity (6 to 64-fold), while 4- and 5-nitroimidazole analogues did not display hypoxia-selective cytotoxicity. All analogues sensitised anoxic HCT-116 human colorectal cells to radiation at non-toxic concentrations. 2-Nitroimidazole analogues provided modest sensitisation due to the relatively low concentrations used while several 5-nitroimidazole analogues provided equivalent sensitisation to misonidazole and etanidazole at similar molar concentrations.

DIAGNOSTIC AGENT FOR INFECTIOUS DISEASES

A diagnostic agent for infectious diseases which is capable of distinguishing among different kinds of bacterial species and which allows simple and non-invasive measurement and/or imaging in a short period of time is provided; and a screening method for a therapeutic agent for infectious diseases caused by microorganisms are provided. A diagnostic agent for infectious diseases caused by nitroimidazole susceptible microorganisms, containing an imidazole derivative or a fused imidazole derivative having at least one nitro group on an imidazole ring, or a labeled form thereof as an active ingredient is provided.

Imidazole derivatives as possible microbicides with dual protection

Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 μM and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 μg/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 μg/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9.

Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents

A series of novel cinnamic acid metronidazole ester derivatives have been designed and synthesized, and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Compound 3h showed the most potent biological activity (IC50 = 0.62 μM for EGFR and IC50 = 2.15 μM for HER-2). Docking simulation was performed to position compound 3h into the EGFR active site to determine the probable binding model. Antiproliferative assay results demonstrated that some of these compounds possessed good antiproliferative activity against MCF-7. Compound 3h with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent.