131885-99-9

Basic information

• Product Name: 1,2-Benzenediamine, 4-(1H-imidazol-1-yl)-5-(trifluoromethyl)-
• CAS NO: 131885-99-9
• Molecular Formula: C10H9F3N4
• Molecular Weight: 242.203
• Mol File: 131885-99-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,2-Benzenediamine, 4-(1H-imidazol-1-yl)-5-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzenediamine, 4-(1H-imidazol-1-yl)-5-(trifluoromethyl)-(131885-99-9)
• EPA Substance Registry System: 1,2-Benzenediamine, 4-(1H-imidazol-1-yl)-5-(trifluoromethyl)-(131885-99-9)

Safety Data

• Hazardous Substances Data: 131885-99-9(Hazardous Substances Data)

Upstream product

• 131885-50-2 5-(imidazol-1-yl)-2-nitro-4-trifluoromethylaniline 
• 400-70-4 2,4-dichloro-5-nitrobenzotrifluoride 
• 35375-74-7 5-chloro-2-nitro-4-(trifluoromethyl)aniline 
• 143151-06-8 4-(1H-imidazol-1-yl)-5-(trifluoromethyl)-2-nitroaniline 
• 400-74-8 2-Fluoro-5-nitrobenzotrifluoride 
• 2357-47-3 4-Fluoro-3-trifluoromethylaniline 
• 143151-01-3 4-fluoro-2-nitro-5-(trifluoromethyl)acetanilide 
• 2145-38-2 4-fluoro-3-(trifluoromethyl)acetanilide 

Relevant articles and documents

Design and synthesis of novel 7-heterocycle-6-trifluoromethyl-3- oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group as superior AMPA receptor antagonists with good physicochemical properties

We describe the design, synthesis, and physicochemical and biological properties of a novel series of 7-heterocycle-6-trifluoromethyl-3- oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group joined through a urethane or urea linkage to the heterocycle at the 7 position. Introduction of the trifluoromethyl group at the 6 position conferred good biological activity, including neuroprotective effects, as well as good physicochemical properties. In terms of α-amino-3-hydroxy-5- methylisoxazole propionate receptor (AMPA-R) affinity, a urea linkage was equivalent to a urethane linkage and a pyrrole ring at the 7 position reduced affinity in comparison with an imidazole ring. Among this series, compound 14h (KRP-199), which has a 4-carboxyphenyl group joined through a urethane linkage to a 7-imidazolyl heterocycle, was found to possess high potency and selectivity for the AMPA-R in vitro and to exhibit good neuroprotective effects in vivo. Furthermore, the compound showed good physicochemical properties, including stability to light and good solubility in aqueous solutions.

6-(1H-imidazol-1-yl)-7-nitro-2,3 (1H,4H)-quinoxalinedione hydrochloride (YM90K) and related compounds: Structure-activity relationships for the AMPA- type non-NMDA receptor

A novel series of quinoxalinediones possessing imidazolyl and related heteroaromatic substituents was synthesized and evaluated for their activity to inhibit [3H]AMPA binding from rat whole brain. From the structure- activity relationships, it was found that the 1H-imidazol-1-yl moiety could function as a bioisostere for the cyano and nitro groups, and that 6-(1H- imidazol-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione (11) showed the most potent activity for the AMPA receptor. Compound 11 was evaluated for selectivity versus other excitatory amino acid receptors, and its action against AMPA at its receptor in the rat striatum was characterized. These data showed that compound 11 was a selective antagonist for the AMPA receptor with a K(i) value of 0.084 μM, being approximately equipotent with 2,3-dihydro-6-nitro- 7-sulfamoylbenzo(f)quinoxaline (3) (NBQX; K(i) = 0.060 μM). Compound 11 was also found to give protection against sound-induced seizure on DBA/2 mice at the minimum effective dose of 3 mg/kg ip (3; 10 mg/kg ip).