194729-10-7

Upstream product

• 197369-14-5 2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetic acid methyl ester 
• 194729-09-4 2-(4-nitro-benzoyl)-4,5-(methylenedioxy)-phenyl acetic acid 
• 53732-94-8 5-(4-Nitrophenyl)-1,3-dioxolo[4,5-g]-isochroman 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 

Downstream Products

• 862457-88-3 C₁₈H₁₃N₃O₂ 
• 194729-29-8 C₁₈H₁₄N₄O₂ 
• 194729-28-7 5-(4-Nitrophenyl)-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2.3]benzodiazepine 
• 862457-91-8 C₁₈H₁₂Br₂N₄O₂ 
• 862457-90-7 8,9-dibromo-5-(4-nitrophenyl)-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine 
• 862457-87-2 (2,2-dimethoxy-ethyl)-[5-(4-nitro-phenyl)-7,9-dihydro-1,3-dioxa-6,7-diaza-cyclohepta[f]inden-8-ylidene]-amine 

Relevant academic research and scientific papers

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

CONDENSED 2,3-BENZODIAZEPINE DERIVATIVES AND THIER USE AS AMPA-RECEPTOR INHIBITORS

Compounds of formula I are described, their production and use in pharmaceutical agents.

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.