2-Methyl-5-nitroimidazol-1-ylacetic acid

Base Information

• Chemical Name: 2-Methyl-5-nitroimidazol-1-ylacetic acid
• CAS No.: 1010-93-1
• Molecular Formula: C6H7 N3 O4
• Molecular Weight: 185.139
• Hs Code.: 2933290090
• UNII: 69IKL472BQ
• DSSTox Substance ID: DTXSID80143626
• Nikkaji Number: J49.310D
• Wikidata: Q27264353
• Metabolomics Workbench ID: 87136
• ChEMBL ID: CHEMBL3544703
• Mol file: 1010-93-1.mol

Synonyms:1-acetic acid-2-methyl-5-nitroimidazole;1-carboxymethylmetronidazole;2-methyl-5-nitroimidazol-1-ylacetic acid;metronidazole-1-acetic acid

Chemical Property of 2-Methyl-5-nitroimidazol-1-ylacetic acid

Chemical Property:

• Vapor Pressure: 7.28E-10mmHg at 25°C
• Melting Point: 176-178 °C
• Boiling Point: 475.9°Cat760mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 241.6°C
• PSA: 100.94000
• Density: 1.6g/cm³
• LogP: 0.70750
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 185.04365571
• Heavy Atom Count: 13
• Complexity: 226

Purity/Quality:

97% ^*data from raw suppliers

2-Methyl-5-nitroimidazole-1-aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(N1CC(=O)O)[N+](=O)[O-]
• General Description: 2-Methyl-5-nitroimidazol-1-ylacetic acid is a derivative of metronidazole, characterized by the presence of a nitroimidazole core with a methyl group at the 2-position and an acetic acid substituent at the 1-position. It serves as a key intermediate in the synthesis of antiparasitic agents, particularly when conjugated with amino acids or their esters, to enhance biological activity. The compound's structure allows for further chemical modifications, making it valuable in the development of novel therapeutics targeting parasitic infections such as amoebiasis and giardiasis. Its derivatives have been evaluated for improved efficacy and reduced cytotoxicity compared to standard metronidazole.

Technology Process of 2-Methyl-5-nitroimidazol-1-ylacetic acid

There total 6 articles about 2-Methyl-5-nitroimidazol-1-ylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.3%

tert-butyl 2-(2-methyl-5-nitroimidazol-1-yl)acetate → 2-methyl-5-nitroimidazole-1-acetic acid (1010-93-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.3390/molecules21121693

Reference yield: 66.0%

metronidazole (443-48-1) → 2-methyl-5-nitroimidazole-1-acetic acid (1010-93-1)

Guidance literature:

With potassium dichromate; sulfuric acid; In water; at 20 ℃; Cooling with ice;

DOI:10.1111/cbdd.13366

Reference yield: 13.0%

2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetaldehyde (56910-52-2) → 2-methyl-5-nitroimidazole-1-acetic acid (1010-93-1)

Guidance literature:

With sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenorthophosphate; In water; tert-butyl alcohol;

upstream raw materials:

metronidazole

ethyl 2-(2-methyl-5-nitro-1H-imidazole-1-yl)acetate

2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetaldehyde

Downstream raw materials:

ethyl 2-(2-methyl-5-nitro-1H-imidazole-1-yl)acetate

N-[3-(3-fluoro-4-{4-[2-(2-methyl-5-nitro-imidazol-1-yl)-acetyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(phenylsulfonyl)acetamide

N-(4-chlorophenylsulfonyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetamide

Refernces

Synthesis of new compounds derived from metronidazole and amino acids and their esters as antiparasitic agents

10.1007/s00044-011-9689-y

The research focuses on the synthesis and evaluation of new compounds derived from metronidazole and amino acids and their esters as potential antiparasitic agents. The synthesis involved a reaction between 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetic acid and various amino acid esters in the presence of N,N'-carbonyldiimidazole (CDI) and triethylamine (TEA), followed by hydrolysis with sodium hydroxide and acidification with hydrochloric acid to obtain the corresponding acids. The synthesized compounds were characterized using elemental analysis and spectroscopic techniques such as 1H-NMR, 13C-NMR, and mass spectrometry. The biological activity of these compounds was assessed through in vitro antiamoebic and antigiardial activity assays, as well as cytotoxicity tests on Hep-2 and Vero cell lines, with metronidazole serving as a standard drug for comparison. The study aimed to identify new derivatives with enhanced antiparasitic activity and lower cytotoxicity, which could contribute to overcoming drug resistance in pathogens.