197004-63-0

Basic information

• Product Name: 1H-Imidazole-1-acetamide,N-(2-hydroxyethyl)-N-methyl-2-nitro-
• Synonyms: TX 1877
• CAS NO: 197004-63-0
• Molecular Formula: C₈H₁₂N₄O₄
• Molecular Weight: 228.21
• Mol File: 197004-63-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-1-acetamide,N-(2-hydroxyethyl)-N-methyl-2-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-1-acetamide,N-(2-hydroxyethyl)-N-methyl-2-nitro-(197004-63-0)
• EPA Substance Registry System: 1H-Imidazole-1-acetamide,N-(2-hydroxyethyl)-N-methyl-2-nitro-(197004-63-0)

Safety Data

• Hazard Codes: A poison.:
• Safety Statements: x." target="_blank">A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.:
• Hazardous Substances Data: 197004-63-0(Hazardous Substances Data)

Usage

Type of compound

Nitroimidazole derivative

Potential uses

Antiparasitic and antibacterial agent

+ Imidazole ring

A five-membered aromatic ring with a nitrogen atom at each end.

+ Acetamide group

A functional group with the structure -CO-NH2, attached to a carbon chain.

+ Nitro group

A functional group with the structure -NO2, consisting of an oxygen-nitrogen-oxygen bond.

+ Hydroxyethyl substituent

An ethyl group (-CH2-CH3) with a hydroxyl group (-OH) attached.

+ Methyl substituent

A single carbon atom with three hydrogen atoms attached (-CH3).

Therapeutic potential

+ Selectively targets hypoxic regions of tumors, making it a potential candidate for cancer therapy.
+ Antimicrobial properties, with potential as a treatment for infections caused by certain parasitic and bacterial pathogens.

Upstream product

• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 22813-31-6 methyl 2-(2-nitro-1H-imidazole-1-yl)acetate 

Relevant articles and documents

Design, synthesis, and radiosensitizing activities of sugar-hybrid hypoxic cell radiosensitizers

We have designed sugar-hybrid TX-1877 derivatives conjugated with sugar moieties including β-glucose (β-Glc), β-galactose (β-Gal), α-mannose (α-Man) and N-acetyl-β-galactosamine (β-GalNAc). Compound 1 (TX-1877) was glycosylated with appropriate peracetylated sugars using BF3-OEt2 to give acetylated sugar-hybrids, 5 (TX-2244), 6 (TX-2245), 7 (TX-2246), and 10 (TX-2243). Removal of the acetyl groups afforded the sugar-hybrids having free hydroxyl groups, 11 (TX-2141), 12 (TX-2218), 13 (TX-2217) and 14 (TX-2068). We evaluated their radiosensitizing activities by an in vitro radiosensitization assay. All free hydroxyl hybrids have lower enhancement ratio (ER) values (ER ≤ 1.43) and lower n-octanol/water partition coefficient (Poct) values (Poct -2) than does 1 (TX-1877, ER = 1.75, Poct: 5.60 × 10-2). All acetylated hybrids have similar Poct values (3.55 × 10-2-1.05 × 10-1) to 1 (TX-1877) and have improved ER values (ER ≥ 1.47) compared to the hybrids having free hydroxyl groups. Among these, 5 (TX-2244) is the most active radiosensitizer (ER = 2.30). We found a good correlation (r = 0.866) between the magnitude of Poct (logPoct) and the ER value of 5 (TX-2244), 6 (TX-2245), 7 (TX-2246), 10 (TX-2243) and 1 (TX-1877), suggesting that increasing the hydrophobicity is reflected in increased in vitro radiosensitizing activity. In the present study, we have succeeded in producing sugar-hybrid hypoxic cell radiosensitizers that have an increased radiosensitizing activity that does not depend on increased hydrophobicity.