Compounds > 4,5-dihydro-7,8-dimethoxy-1-phenyl-3h-2,3-benzodiazepin-4-one
Page last updated: 2024-11-11

4,5-dihydro-7,8-dimethoxy-1-phenyl-3h-2,3-benzodiazepin-4-one

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Description

4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-one: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9860972
CHEMBL ID279064
SCHEMBL ID5488342
MeSH IDM0407919

Synonyms (8)

Synonym
CHEMBL279064
41148-42-9
SCHEMBL5488342
7,8-dimethoxy-1-phenyl-3,5-dihydro-4h-2,3-benzodiazepin-4-one
CIBFDTUUNLMFMC-UHFFFAOYSA-N
DTXSID20432021
4,5-dihydro-7,8-dimethoxy-1-phenyl-3h-2,3-benzodiazepin-4-one
ortho dimethoxybenzo-phenyldiazotropone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
protein bindingGlutamate receptor 4Mus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (48)

Assay IDTitleYearJournalArticle
AID113603Anticonvulsant activity against clonic seizures induced by icv injection of AMPA in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID114472Audiogenic seizures after concomitant treatment with Flumazenil (8.24 uM) in DBA / 2 mice tonic phase1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113461Anticonvulsant activity against clonic phase of the audiogenic seizures in DBA / 2 mice 30 min after ip administration at a dose range 10-100 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113626Anticonvulsant activity against tonic phase of the audiogenic seizures in DBA / 2 mice 30 min after ip administration at a dose range 10-100 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID53447Evaluated for anticonvulsant property in DBA/2 mice against Locomotion assessed by Rotarod test (ip administration); value ranges from 87.3-2312000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones.
AID231693Ratio between TD50 and ED50 from the clonic phase of the audiogenic seizures was determined1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID113023In vivo anticonvulsant activity was measured as median effective dose required to prevent clonic phase of seizure in DBA/2 mice2004Journal of medicinal chemistry, Mar-25, Volume: 47, Issue:7
QSAR study of anticonvulsant negative allosteric modulators of the AMPA receptor.
AID234046Therapeutic index (TD50/ED50) from the clonic phase of the audiogenic seizures1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID114476Audiogenic seizures after pretreatment with Aniracetam in DBA / 2 mice tonic phase at a dose range of 33-300 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113625Anticonvulsant activity against tonic phase of the audiogenic seizures after pretreatment with aniracetam in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID114070Pentylenetetrazole-induced seizures in Swiss mice after 45 min pretreatment at a dose range 10-100 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113624Anticonvulsant activity against tonic phase of the audiogenic seizures after concomitant with flumazenil at 8.24 umol dose in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113774Anticonvulsant activity against tonic seizures induced by icv injection of AMPA in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113605Anticonvulsant activity against maximal electroshock (MES) seizures in swiss mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113459Anticonvulsant activity against clonic phase of the audiogenic seizures after concomitant with flumazenil at 8.24 umol dose in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113024In vivo anticonvulsant activity was measured as median effective dose required to prevent tonic phase of seizure in DBA/2 mice2004Journal of medicinal chemistry, Mar-25, Volume: 47, Issue:7
QSAR study of anticonvulsant negative allosteric modulators of the AMPA receptor.
AID129621Compound was evaluated for anticonvulsant activity against MES induced seizures(tonic phase) in swiss mice1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID235208Therapeutic index is the ratio between TD50 and ED50 (from the clonic phase of the audiogenic seizures)2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones.
AID129633Compound was evaluated for anticonvulsant activity against audiogenic seizures in DBA/2 mice( clonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID114474Audiogenic seizures after pretreatment with Aniracetam in DBA / 2 mice clonic phase at a dose range of 33-300 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID53436Evaluated for anticonvulsant property in DBA/2 mice against Audiogenic seizures during tonic phase (ip administration); value ranges from 24.8-40.62000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones.
AID129619Compound was evaluated for anticonvulsant activity against AMPA induced seizures in DBA/2 mice( clonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID235218Therapeutic index it is the ratio between TD50 and ED50 (from the clonic phase of the audiogenic seizures)1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID129634Compound was evaluated for anticonvulsant activity against audiogenic seizures in DBA/2 mice( tonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID129628Compound was evaluated for anticonvulsant activity against audiogenic induced seizures after pretreatment with aniracetam (tonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID114469Audiogenic seizures after concomitant treatment with Flumazenil (24.72 uM) in DBA / 2 mice clonic phase1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113614Anticonvulsant activity against the clonic seizures induced by icv injection of AMPA in DBA / 2 mice at a dose range of 10-200 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID628752Inhibition of bovine aortic PDE4 using cAMP as substrate in presence of cGMP2011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
New PDE4 inhibitors based on pharmacophoric similarity between papaverine and tofisopam.
AID113458Anticonvulsant activity against clonic phase of the audiogenic seizures after concomitant with flumazenil at 24.72 umol dose in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID212209Compound was evaluated for toxic dose on locomotor assessed by rotarod test in mice1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID129622Compound was evaluated for anticonvulsant activity against PTZ induced seizures (clonic phase) in swiss mice1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID113621Anticonvulsant activity against the tonic seizures induced by icv injection of AMPA in DBA / 2 mice at a dose range of 10-200 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID53429Evaluated for anticonvulsant property in DBA/2 mice against Audiogenic seizures during clonic phase (ip administration); value ranges from 26.0-44.22000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones.
AID114470Audiogenic seizures after concomitant treatment with Flumazenil (24.72 uM) in DBA / 2 mice tonic phase1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID113607Anticonvulsant activity against pentylenetetrazole (PTZ)-induced seizures in swiss mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113616Anticonvulsant activity against the maximal electroshock in Swiss mice after 45 minutes pretreatment at a dose range 10-100 uM/kg1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID212213Dose which induced 50% of mice to fall from the rotarod1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113460Anticonvulsant activity against clonic phase of the audiogenic seizures after pretreatment with aniracetam in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID129623Compound was evaluated for anticonvulsant activity against audiogenic induced seizures after pretreatment with aniracetam (clonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID20516Relative lipophilicity of compound1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID212215Motor toxicity in 50% of mice on locomotion assessed by Rotarod test following 30 min ip administration1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID114471Audiogenic seizures after concomitant treatment with Flumazenil (8.24 uM) in DBA / 2 mice clonic phase1997Journal of medicinal chemistry, Apr-11, Volume: 40, Issue:8
1-Aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists.
AID129620Compound was evaluated for anticonvulsant activity against AMPA induced seizures in DBA/2 mice( tonic phase)1998Bioorganic & medicinal chemistry letters, Apr-21, Volume: 8, Issue:8
7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists.
AID113451Anticonvulsant activity against audiogenic seizures in DBA/2 mice (value required to prevent tonic phases of seizures).1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID20517Relative lipophilicity1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113450Anticonvulsant activity against audiogenic seizures in DBA/2 mice (value required to prevent clonic phases of seizures).1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID113623Anticonvulsant activity against tonic phase of the audiogenic seizures after concomitant with flumazenil at 24.72 umol dose in DBA/2 mice1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists.
AID20515Relative Lipophilicity measured by reversed-phase high performance thin-layer chromatography (RP-HPTLC)2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-[1,2,4]triazolo[4,5-c][2,3]benzodiazepin-3(2H)-ones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (42.86)18.2507
2000's3 (42.86)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.19 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethaverine
ethaverine: tetraethyl homolog of papaverine; smooth muscle relaxant; RN given refers to parent cpd; structure		2.0610isoquinolines
gyki 52466
GYKI 52466: an AMPA (non-NMDA) receptor antagonist; structure given in first source		3.150benzodiazepine
papaverine
Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.		2.0610benzylisoquinoline alkaloid;
dimethoxybenzene;
isoquinolines		antispasmodic drug;
vasodilator agent
tofisopam
tofisopam: structure; dextofisopam is the R-enantiomer of tofisopam & antidiarrheal		2.0610organic molecular entity
girisopam
[no description available]		2.0610
cfm 2
CFM 2: structure in first source		3.150benzodiazepine
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		02.9140
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		02.9140