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

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

SUBSTITUTED 2,3-BENZODIAZEPIN-4-ONES AND THE USE THEREOF

The invention relates to substituted 2,3-benzodiazepin-4-ones which are antagonists or positive modulators of AMPA receptors, and the use thereof for treating, preventing or ameliorating neuronal loss associated with stroke, global and focal ischemia, CNS

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

SUBSTITUTED 2,3-BENZODIAZEPIN-4-ONES AND THE USE THEREOF

The invention relates to substituted 2,3-benzodiazepin-4-ones which are antagonists or positive modulators of AMPA receptors, and the use thereof for treating, preventing or ameliorating neuronal loss associated with stroke, global and focal ischemia, CNS trauma, hypoglycemia and surgery, as well as treating or ameliorating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease, Parkinson's disease and Down's syndrome, treating, preventing or ameliorating the adverse consequences of the overstimulation of the excitatory amino acids, treating or ameliorating anxiety, psychosis, convulsions, chronic pain, glaucoma, CMV retinitis, urinary incontinence, muscular spasm and inducing anesthesia, as well as for treating or ameliorating the adverse consequences of excitatory amino acid deficiency such as schizophrenia, Alzheimer's disease and malnutrition and neural maldevelopment, and as cognition enhancers. The invention also is directed to the process for the preparation of the substituted 2,3-benzodiazepin-4-ones.

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.