Page last updated: 2024-11-11

ap 2238

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID9844749
CHEMBL ID75121
MeSH IDM0451421

Synonyms (13)

Synonym
ap-2238
3-(4-{[benzyl(methyl)amino]methyl}phenyl)-6,7-dimethoxy-2h-chromen-2-one
3-(4-{[benzyl(methyl)amino]methyl}-phenyl)-6,7-dimethoxy-2h-2-chromenone
bdbm10949
ap2238
chembl75121 ,
553681-56-4
unii-545225e0bc
2h-1-benzopyran-2-one, 6,7-dimethoxy-3-(4-((methyl(phenylmethyl)amino)methyl)phenyl)-
545225e0bc ,
Q27261165
3-[4-[[benzyl(methyl)amino]methyl]phenyl]-6,7-dimethoxychromen-2-one
AKOS040750535
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)0.04000.00000.94539.9400AID1379010
CholinesteraseHomo sapiens (human)IC50 (µMol)48.90000.00001.559910.0000AID1796570; AID296910; AID44295; AID462783; AID640564
CholinesteraseHomo sapiens (human)Ki0.02170.00001.51739.7300AID1796570
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)IC50 (µMol)48.90000.00031.38338.4000AID44295
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)8.92730.00000.933210.0000AID1360320; AID1486228; AID1632240; AID1796570; AID241141; AID296909; AID314091; AID31502; AID315645; AID462782
AcetylcholinesteraseHomo sapiens (human)Ki0.02170.00001.27869.7300AID1796570; AID31621
CholinesteraseEquus caballus (horse)IC50 (µMol)12.36000.00002.22149.4000AID1379011
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID31777Tested for inhibition of AChE-induced Abeta aggregation in the peripheral sites of the human enzyme at a concentration of 100 uM2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function lead for Alzheimer's disease therapy.
AID314093Inhibition of human AchE-induced amyloid beta aggregation at 100 uM2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Multi-target-directed ligands to combat neurodegenerative diseases.
AID31621Inhibitory potency was evaluated against recombinant human AChE2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function lead for Alzheimer's disease therapy.
AID462783Inhibition of human BuChE preincubated for 20 mins before substrate addition by Ellman's method2010Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5
Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238.
AID462782Inhibition of human recombinant AChE preincubated for 20 mins before substrate addition by Ellman's method2010Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5
Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238.
AID462787Inhibition of amyloid beta (1-42) self-aggregation at 10 uM after 24 hrs by thioflavin T-based fluorometric assay2010Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5
Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238.
AID314091Inhibition of human AchE2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Multi-target-directed ligands to combat neurodegenerative diseases.
AID296909Inhibition of human recombinant AChE2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives.
AID1379010Inhibition of electric eel AChE using acetylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition measured up to 180 secs by spectrophotometric analysis2017European journal of medicinal chemistry, Oct-20, Volume: 139Novel cinnamamide-dibenzylamine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer's disease.
AID1379019Antioxidant activity assessed as inhibition of AAPH-induced peroxyl radical generation measured as trolox equivalent preincubated for 15 mins followed by AAPH addition measured every min for 120 mins by ORAC-FL assay2017European journal of medicinal chemistry, Oct-20, Volume: 139Novel cinnamamide-dibenzylamine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer's disease.
AID640564Inhibition of BuChE2012Bioorganic & medicinal chemistry, Feb-01, Volume: 20, Issue:3
A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease.
AID241141Inhibitory concentration Acetylcholinesterase2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors.
AID1379012Selectivity index, ratio of IC50 for equine serum BChE to IC50 for electric eel AChE2017European journal of medicinal chemistry, Oct-20, Volume: 139Novel cinnamamide-dibenzylamine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer's disease.
AID296910Inhibition of human recombinant BChE2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives.
AID44295Inhibitory potency was evaluated against isolated Butyrylcholinesterase2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function lead for Alzheimer's disease therapy.
AID1632240Inhibition of acetylcholinesterase (unknown origin)2016Bioorganic & medicinal chemistry, 10-01, Volume: 24, Issue:19
Coumarin derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies.
AID1360320Inhibition of human AChE2018European journal of medicinal chemistry, Jul-15, Volume: 155Novel tetrahydrocarbazole benzyl pyridine hybrids as potent and selective butryl cholinesterase inhibitors with neuroprotective and β-secretase inhibition activities.
AID296911Inhibition of human AChE-mediated beta amyloid 1-40 aggregation at 100 uM2007Journal of medicinal chemistry, Aug-23, Volume: 50, Issue:17
Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives.
AID31502Inhibitory potency was evaluated against recombinant human AChE2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function lead for Alzheimer's disease therapy.
AID462784Selectivity ratio of IC50 for human BuChE to human recombinant AChE2010Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5
Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238.
AID315645Inhibition of human recombinant AChE by Ellman method2008Bioorganic & medicinal chemistry letters, Jan-01, Volume: 18, Issue:1
Multi-target-directed coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds.
AID1379011Inhibition of equine serum BChE using S-butyrylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition measured up to 180 secs by spectrophotometric analysis2017European journal of medicinal chemistry, Oct-20, Volume: 139Novel cinnamamide-dibenzylamine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer's disease.
AID1379020Inhibition of HFIP pretreated amyloid beta (1 to 42) (unknown origin) self-aggregation at 20 uM after 48 hrs by thioflavin T fluorescence assay relative to control2017European journal of medicinal chemistry, Oct-20, Volume: 139Novel cinnamamide-dibenzylamine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer's disease.
AID462786Inhibition of human recombinant AChE-induced amyloid beta (1-40) aggregation at 100 uM by thioflavin T fluorescence assay2010Bioorganic & medicinal chemistry, Mar-01, Volume: 18, Issue:5
Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238.
AID1486228Inhibition of recombinant human AChE using acetylthiocholine as substrate by Ellman's method2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
Synthesis, docking study and neuroprotective effects of some novel pyrano[3,2-c]chromene derivatives bearing morpholine/phenylpiperazine moiety.
AID1796570Cholinesterase Inhibition Assay from Article 10.1021/jm0340602: \\3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
3-(4-[[Benzyl(methyl)amino]methyl]phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: a dual function lead for Alzheimer's disease therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (45.45)29.6817
2010's6 (54.55)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: 11.98

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 Index11.98 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (18.18%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (81.82%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]