178616-26-7

Basic information

• Product Name: 1-(4'-AMINOPHENYL)-3,5-DIHYDRO-7,8-DIMETHOXY-4H-2,3-BENZODIAZEPIN-4-ONE
• Synonyms: CFM-2;1-(4'-AMINOPHENYL)-3,5-DIHYDRO-7,8-DIMETHOXY-4H-2,3-BENZODIAZEPIN-4-ONE;4H-2,3-Benzodiazepin-4-one,1-(4-aminophenyl)-3,5-dihydro-7,8-dimethoxy-
• CAS NO: 178616-26-7
• Molecular Formula: C₁₇H₁₇N₃O₃
• Molecular Weight: 311.34
• Product Categories: Glutamate receptor
• Mol File: 178616-26-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.32g/cm³
• Storage Temp.: Store at RT
• CAS DataBase Reference: 1-(4'-AMINOPHENYL)-3,5-DIHYDRO-7,8-DIMETHOXY-4H-2,3-BENZODIAZEPIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-AMINOPHENYL)-3,5-DIHYDRO-7,8-DIMETHOXY-4H-2,3-BENZODIAZEPIN-4-ONE(178616-26-7)
• EPA Substance Registry System: 1-(4'-AMINOPHENYL)-3,5-DIHYDRO-7,8-DIMETHOXY-4H-2,3-BENZODIAZEPIN-4-ONE(178616-26-7)

Safety Data

• Hazardous Substances Data: 178616-26-7(Hazardous Substances Data)

Usage

Uses

CFM-2 is a non-competitive antagonist of the AMPA receptors.

Biological Activity

Novel, selective non-competitive AMPA antagonist. Highly potent, long-acting anticonvulsant.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 187940-06-3 [4,5-Dimethoxy-2-(4-nitro-benzoyl)-phenyl]-acetic acid 
• 92774-40-8 3,4-dihydro-6,7-dimethoxy-1-(4-nitrophenyl)-1H-isochromene 
• 187940-12-1 7,8-Dimethoxy-1-(4-nitro-phenyl)-3,5-dihydro-benzo[d][1,2]diazepin-4-one 

Relevant articles and documents

Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists

2,3-Benzodiazepines represent a class of heterocyclic compounds that interact with AMPA-type glutamate receptors in a noncompetitive manner. These compounds have attracted great interest for their pharmacological effects against acute and chronic neurodeg

1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: Novel AMPA receptor antagonists

Our previous publication (Eur. J. Pharmacol. 1995, 294, 411-422) reported preliminary chemical and biological studies of some 2,3- benzodiazepines, analogues of 1-(4-aminophenyl)-4-methyl-7,8- (methylenedioxy)-5H-2,3-benzodiazepine (1, GYKI 52466), which have been shown to possess significant anticonvulsant activity. This paper describes the synthesis of new 1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones and the evaluation of their anticonvulsant effects. The observed findings extend the structure-activity relationships previously suggested for this class of anticonvulsants. The seizures were evoked both by means of auditory stimulation in DBA/2 mice and by pentylenetetrazole or maximal electroshock in Swiss mice. 1-(4'-Aminophenyl)- (38) and 1-(3'-aminophenyl)-3,5-dihydro- 7,8-dimethoxy-4H-2,3-benzodiazepin-4-one (39), the most active compounds of the series, proved to be more potent than 1 in all tests employed. In particular, the ED50 values against tonus evoked by auditory stimulation were 12.6 μmol/kg for derivative 38, 18.3 μmol/kg for 39, and 25.3 μmol/kg for 1. Higher doses were necessary to block tonic extension induced both by maximal electroshock and by pentylenetetrazole. In addition these compounds exhibited anticonvulsant properties that were longer lasting than those of compound 1 and were less toxic. The novel 2,3-benzodiazepines were also investigated for a possible correlation between their anticonvulsant activities against convulsions induced by 2-amino-3-(3-hydroxy-5- methylisoxazol-4-yl)propionic acid (AMPA) and their affinities for benzodiazepine receptors (BZR). The 2,3-benzodiazepines did not affect the binding of [3H]flumazenil to BZR, and conversely, their anticonvulsant effects were not reversed by flumazenil. On the other hand the 2,3- benzodiazepines antagonized seizures induced by AMPA and aniracetam in agreement with an involvement of the AMPA receptor. In addition, both the derivative 38 and the compound 1 markedly reduced the AMPA receptor-mediated membrane currents in guinea-pig olfactory cortical neurons in vitro in a noncompetitive manner. The derivatives 25 and 38-40 failed to displace specific ligands from N-methyl-D-aspartate (NMDA), AMPA/kainate, or metabotropic glutamate receptors.