Page last updated: 2024-11-12

n-(4-chloro-2-((1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)methyl)phenyl)-2-hydroxybenzamide

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Description

N-(4-chloro-2-((1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl)phenyl)-2-hydroxybenzamide: a positive allosteric modulator of mGluR5; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9931205
CHEMBL ID366217
SCHEMBL ID1821580
MeSH IDM0460703

Synonyms (27)

Synonym
gtpl1423
n-[4-chloro-2-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]-2-hydroxybenzamide
n-(4-chloro-2-((1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)methyl)phenyl)-2-hydroxybenzamide
cppha
n-[4-chloro-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-phenyl]-2-hydroxy-benzamide
bdbm50156070
n-(4-chloro-2-((1,3-dioxoisoindolin-2-yl)methyl)phenyl)-2-hydroxybenzamide
n-(4-chloro-2-[(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)methyl]phenyl)-2-hydroxybenzamide
CHEMBL366217 ,
BCP9000553
693288-97-0
n-{4-chloro-2-[(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)methyl]phenyl}-2-hydroxybenzamide
UFOUABRZSDGGAZ-UHFFFAOYSA-N
CS-1640
HY-14612
AKOS022184338
SCHEMBL1821580
n-[4-chloro-2-[(1,3-dihydro-1,3-dioxo-2h-isoindol-2-yl)methyl]phenyl]-2-hydroxybenzamide
DTXSID80433014
cppha, >=98% (hplc)
FT-0729923
Q27076912
BCP09918
A853067
BC171188
AS-83211
E98868
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Metabotropic glutamate receptor 5Rattus norvegicus (Norway rat)IC50 (µMol)0.93000.00000.52627.9700AID1325979
Metabotropic glutamate receptor 5Homo sapiens (human)IC50 (µMol)10.00000.00050.439410.0000AID1325977
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Metabotropic glutamate receptor 5Rattus norvegicus (Norway rat)EC50 (µMol)1.00000.00151.653710.0000AID305983
Metabotropic glutamate receptor 5Homo sapiens (human)EC50 (µMol)0.23330.00190.61454.1000AID240173; AID305981; AID773852
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
desensitization of G protein-coupled receptor signaling pathwayMetabotropic glutamate receptor 5Homo sapiens (human)
regulation of DNA-templated transcriptionMetabotropic glutamate receptor 5Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 5Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayMetabotropic glutamate receptor 5Homo sapiens (human)
phospholipase C-activating G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 5Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 5Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 5Homo sapiens (human)
learning or memoryMetabotropic glutamate receptor 5Homo sapiens (human)
learningMetabotropic glutamate receptor 5Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 5Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 5Homo sapiens (human)
positive regulation of long-term neuronal synaptic plasticityMetabotropic glutamate receptor 5Homo sapiens (human)
synapse organizationMetabotropic glutamate receptor 5Homo sapiens (human)
positive regulation of calcium-mediated signalingMetabotropic glutamate receptor 5Homo sapiens (human)
cognitionMetabotropic glutamate receptor 5Homo sapiens (human)
regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 5Homo sapiens (human)
regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 5Homo sapiens (human)
cellular response to amyloid-betaMetabotropic glutamate receptor 5Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 5Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionMetabotropic glutamate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityMetabotropic glutamate receptor 5Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 5Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 5Homo sapiens (human)
protein tyrosine kinase activator activityMetabotropic glutamate receptor 5Homo sapiens (human)
A2A adenosine receptor bindingMetabotropic glutamate receptor 5Homo sapiens (human)
identical protein bindingMetabotropic glutamate receptor 5Homo sapiens (human)
protein tyrosine kinase bindingMetabotropic glutamate receptor 5Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 5Homo sapiens (human)
neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 5Homo sapiens (human)
G protein-coupled receptor activity involved in regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
dendriteMetabotropic glutamate receptor 5Homo sapiens (human)
cytoplasmMetabotropic glutamate receptor 5Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 5Homo sapiens (human)
dendritic spineMetabotropic glutamate receptor 5Homo sapiens (human)
dendritic shaftMetabotropic glutamate receptor 5Homo sapiens (human)
astrocyte projectionMetabotropic glutamate receptor 5Homo sapiens (human)
Schaffer collateral - CA1 synapseMetabotropic glutamate receptor 5Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 5Homo sapiens (human)
postsynaptic density membraneMetabotropic glutamate receptor 5Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID719494Selectivity ratio of EC50 for human mGlu5 receptor expressed in HEK293 cells to EC50 for rat mGlu5 receptor expressed in HEK293 cells2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Discovery and SAR of a novel series of non-MPEP site mGlu₅ PAMs based on an aryl glycine sulfonamide scaffold.
AID1325983Selectivity ratio of EC50 for mGlu5 receptor CPPHA allosteric binding site mutant (unknown origin) expressed in HEK cells to EC50 for mGlu5 receptor (unknown origin)2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Development of 1
AID305982Activity at human mGluR5 expressed in CHO cells assessed as potentiation of glutamate response by FLIPR assay relative to glutamate2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Challenges in the development of mGluR5 positive allosteric modulators: the discovery of CPPHA.
AID1325979Displacement of [3H]-MethoxyPEPy from mGlu5 receptor in primary rat astrocytes after 8 hrs by micro beta scintillation counting analysis2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Development of 1
AID420119Activity at human mGluR5 transiently transfected in BHK cells assessed as decrease in maximum response of L-glutamate for calcium flux at 1500 nM by FLIPR assay2009Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12
Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator.
AID1325977Displacement of [3H]-MethoxyPEPy from human mGlu5 receptor expressed in HEK293 cell membranes after 8 hrs by micro beta scintillation counting analysis2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Development of 1
AID420104Activity at human mGluR5 transiently transfected in BHK cells assessed as decrease in maximum response of L-glutamate for calcium flux at 15 nM by FLIPR assay2009Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12
Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator.
AID240173Effective concentration against metabotropic glutamate receptor 5 of human transfected into CHO cells2004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Discovery of positive allosteric modulators for the metabotropic glutamate receptor subtype 5 from a series of N-(1,3-diphenyl-1H- pyrazol-5-yl)benzamides that potentiate receptor function in vivo.
AID1325981Selectivity ratio of EC50 for mGlu5 receptor MPEP allosteric binding site mutant (unknown origin) expressed in HEK cells to EC50 for mGlu5 receptor (unknown origin)2016ACS medicinal chemistry letters, Dec-08, Volume: 7, Issue:12
Development of 1
AID305983Activity at rat mGluR5 expressed in CHO cells assessed as potentiation of glutamate response by FLIPR assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Challenges in the development of mGluR5 positive allosteric modulators: the discovery of CPPHA.
AID773852Positive allosteric modulation of human mGluR52013Journal of medicinal chemistry, Oct-24, Volume: 56, Issue:20
Exploration of allosteric agonism structure-activity relationships within an acetylene series of metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulators (PAMs): discovery of 5-((3-fluorophenyl)ethynyl)-N-(3-methyloxetan-3-yl)picolinamide
AID343891Induction of rat mGluR5 activation expressed in HEK293A cells assessed as maximal response in presence of glutamate2008Bioorganic & medicinal chemistry letters, Jul-15, Volume: 18, Issue:14
Synthesis and SAR of a mGluR5 allosteric partial antagonist lead: unexpected modulation of pharmacology with slight structural modifications to a 5-(phenylethynyl)pyrimidine scaffold.
AID252325Fold potentiation in CHO cells overexpressing human metabotropic glutamate receptor 52004Journal of medicinal chemistry, Nov-18, Volume: 47, Issue:24
Discovery of positive allosteric modulators for the metabotropic glutamate receptor subtype 5 from a series of N-(1,3-diphenyl-1H- pyrazol-5-yl)benzamides that potentiate receptor function in vivo.
AID305981Activity at human mGluR5 expressed in CHO cells assessed as potentiation of glutamate response by FLIPR assay2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Challenges in the development of mGluR5 positive allosteric modulators: the discovery of CPPHA.
AID420103Activity at human mGluR5 transiently transfected in BHK cells assessed as decrease in maximum response of L-glutamate for calcium flux at 150 nM by FLIPR assay2009Bioorganic & medicinal chemistry letters, Jun-15, Volume: 19, Issue:12
Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator.
AID1346269Human mGlu5 receptor (Metabotropic glutamate receptors)2004The Journal of pharmacology and experimental therapeutics, May, Volume: 309, Issue:2
A novel selective allosteric modulator potentiates the activity of native metabotropic glutamate receptor subtype 5 in rat forebrain.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (71.43)29.6817
2010's4 (28.57)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: 11.63

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 Index11.63 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]