197368-47-1

Basic information

• Product Name: 1-(4-fluorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one
• Synonyms: 1-(4-fluorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one
• CAS NO: 197368-47-1
• Molecular Weight: 298.273
• Mol File: 197368-47-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(4-fluorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-fluorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one(197368-47-1)
• EPA Substance Registry System: 1-(4-fluorophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one(197368-47-1)

Safety Data

• Hazardous Substances Data: 197368-47-1(Hazardous Substances Data)

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 
• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 862457-79-2 5-(4-fluoro-phenyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochromene 
• 862457-81-6 [6-(4-fluoro-benzoyl)-benzo[1,3]dioxol-5-yl]-acetic acid 
• 197369-12-3 methyl 2-(4-fluorobenzoyl)-4,5-methylenedioxyphenylacetate 

Downstream Products

• 862457-83-8 5-(4-fluorophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-8(9H)-thione 

Relevant articles and documents

Novel α-amino-3-hydroxy-5-methyl-4-isoxazole propionate (AMPA) receptor antagonists of 2,3-benzodiazepine type: Chemical synthesis, in vitro characterization, and in vivo prevention of acute neurodegeneration

Under pathophysiological conditions, α-amino-3-hydroxy-5-methyl-4- isoxazole propionate (AMPA) receptor activation is considered to play a key role in several disorders of the central nervous system. In the search for AMPA receptor antagonists, the synthe

Synthesis and anticonvulsant activity of new 2,3-benzodiazepines as AMPA receptor antagonists

Novel 1-aryl-3,5-dihydro-7,8-methylenedioxy-4H-2,3-benzodiazepin-4-ones (12a-j) were prepared and their anticonvulsant effects were evaluated by using various models of experimental epilepsy. The seizures were evoked both by means of auditory stimulation

Synthesis of 7,8-(methylenedioxy)-1-phenyl-3,5-dihydro-4H-2,3- benzodiazepin-4-ones as novel and potent noncompetitive AMPA receptor antagonists

A group of 7,8-(methylenedioxy)-1-phenyl-3,5-dihydro-4H-2,3- benzodiazepin-4-ones was synthesized and assayed for antagonism of rat brain α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptors expressed in Xenopus oocytes. The benzodiazepinones inhibited AMPA-activated membrane current responses in a manner consistent with noncompetitive, allosteric inhibition of the receptor-channel complex. The most potent compound in the series was 1-(4-aminophenyl)-7,8-(methylenedioxy)-3,5- dihydro-4H-2,3-benzodiazepin-4-one (6), which had an IC50 of 2.7 μM. For comparison, the reference compound GYKI 52466 (2) had an IC50 of 6.9 μM. Compound 6 also had potent anticonvulsant activity in a mouse maximum electroshock-induced seizure (MES) assay: the ED50 was 2.8 mg/kg iv, whereas the ED50 for GYKI 52466 was 4.6 mg/kg iv. In contrast to a previous report, the 7,8-dimethoxy analogue of 6 was a low-potency AMPA antagonist (IC50 > 100 μM) and weak anticonvulsant (ED60 > 10 mg/kg iv). The benzodiazepinones described herein are potent noncompetitive AMPA receptor antagonists that could have therapeutic potential as anticonvulsants and neuroprotectants.