Page last updated: 2024-11-09

2,5-dimethoxy-n-(quinolin-3-yl)benzenesulfonamide

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Description

2,5-dimethoxy-N-(quinolin-3-yl)benzenesulfonamide: a tissue-nonspecific alkaline phosphatase inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2931238
CHEMBL ID567850
CHEBI ID120462
SCHEMBL ID643754
MeSH IDM0541688

Synonyms (32)

Synonym
OPREA1_133837
IFLAB1_005042
MLS-0038949.0004
MLS-0038949.0005
OPREA1_546815
2,5-dimethoxy-n-3-quinolinylbenzenesulfonamide
smr000071743
MLS000088377
MLS-0038949.0003
ml028
MLS-0038949.0002
MLS-0038949.0001
CHEBI:120462
AKOS000601138
HMS1426F04
CHEMBL567850 ,
bdbm50299523
cid_2931238
2,5-dimethoxy-n-(quinolin-3-yl)benzenesulfonamide
2,5-dimethoxy-n-quinolin-3-ylbenzenesulfonamide
HMS2360K19
AP-263/41417798
SCHEMBL643754
cambridge id 7234072
2,5-dimethoxy-n-(3-quinolinyl)benzenesulfonamide
Q27208308
Z237649750
benzenesulfonamide,2,5-dimethoxy-n-3-quinolinyl-
496014-13-2
benzenesulfonamide, 2,5-dimethoxy-n-3-quinolinyl-
2,5-dimethoxy-n-(quinolin-3-yl)benzene-1-sulfonamide
EN300-6493135

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Critical structural requirements for activity were determined, and the compounds were subsequently profiled for in vitro activity and bioavailability parameters including metabolic stability and permeability."( Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
Brown, B; Cosford, ND; Dahl, R; Mangravita-Novo, A; Millán, JL; Mostofi, YS; Narisawa, S; O'Neill, WC; Sergienko, EA; Simao, AM; Smith, LH; Su, Y; Vicchiarelli, M; Yang, L, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quinolinesA class of aromatic heterocyclic compounds each of which contains a benzene ring ortho fused to carbons 2 and 3 of a pyridine ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency20.73290.000811.382244.6684AID686978; AID686979
IDH1Homo sapiens (human)Potency23.10930.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency10.00000.035520.977089.1251AID504332
chromobox protein homolog 1Homo sapiens (human)Potency89.12510.006026.168889.1251AID540317
survival motor neuron protein isoform dHomo sapiens (human)Potency0.15850.125912.234435.4813AID1458
lamin isoform A-delta10Homo sapiens (human)Potency6.30960.891312.067628.1838AID1487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
alkaline phosphatase, tissue-nonspecific isozyme isoform 1 preproproteinHomo sapiens (human)IC50 (µMol)0.35870.125016.260374.8000AID1056; AID1941; AID518
VifHuman immunodeficiency virus 1IC50 (µMol)100.00000.270034.0015100.0000AID1117319
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)IC50 (µMol)100.00000.270026.3638100.0000AID1117319
alkaline phosphatase, germ cell type preproproteinHomo sapiens (human)IC50 (µMol)100.00000.110011.386267.2000AID1017; AID1512
Alkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)IC50 (µMol)1.18080.01502.24078.6000AID1372334; AID1372335; AID440259; AID440269; AID440270; AID440271
Alkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)Ki0.46500.34000.46500.5900AID440272; AID440273
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00053.314249.5000AID1017
Phospholipase A-2-activating proteinHomo sapiens (human)IC50 (µMol)100.00000.01101.53702.5000AID440264
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
skeletal system developmentAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
osteoblast differentiationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
endochondral ossificationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
developmental process involved in reproductionAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
cellular homeostasisAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
bone mineralizationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to lipopolysaccharideAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to insulinAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to vitamin DAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to vitamin B6Alkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to macrophage colony-stimulating factorAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
pyridoxal phosphate metabolic processAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to antibioticAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to glucocorticoidAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
phosphate ion homeostasisAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
calcium ion homeostasisAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
cellular response to organic cyclic compoundAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
cementum mineralizationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
positive regulation of cold-induced thermogenesisAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
futile creatine cycleAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
inhibition of non-skeletal tissue mineralizationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
response to sodium phosphateAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
dephosphorylationAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
dephosphorylationIntestinal-type alkaline phosphataseHomo sapiens (human)
phospholipid metabolic processPhospholipase A-2-activating proteinHomo sapiens (human)
prostaglandin metabolic processPhospholipase A-2-activating proteinHomo sapiens (human)
inflammatory responsePhospholipase A-2-activating proteinHomo sapiens (human)
signal transductionPhospholipase A-2-activating proteinHomo sapiens (human)
nervous system developmentPhospholipase A-2-activating proteinHomo sapiens (human)
macroautophagyPhospholipase A-2-activating proteinHomo sapiens (human)
positive regulation of phospholipase A2 activityPhospholipase A-2-activating proteinHomo sapiens (human)
ubiquitin-dependent protein catabolic process via the multivesicular body sorting pathwayPhospholipase A-2-activating proteinHomo sapiens (human)
cellular response to lipopolysaccharidePhospholipase A-2-activating proteinHomo sapiens (human)
negative regulation of protein K63-linked ubiquitinationPhospholipase A-2-activating proteinHomo sapiens (human)
positive regulation of synaptic vesicle recyclingPhospholipase A-2-activating proteinHomo sapiens (human)
positive regulation of dendrite extensionPhospholipase A-2-activating proteinHomo sapiens (human)
positive regulation of neuron migrationPhospholipase A-2-activating proteinHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processPhospholipase A-2-activating proteinHomo sapiens (human)
ubiquitin recyclingPhospholipase A-2-activating proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
alkaline phosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
inorganic diphosphate phosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
calcium ion bindingAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
pyrophosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
ATP hydrolysis activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
pyridoxal phosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
ADP phosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
phosphoamidase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
phosphoethanolamine phosphatase activityAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
magnesium ion bindingIntestinal-type alkaline phosphataseHomo sapiens (human)
protease bindingIntestinal-type alkaline phosphataseHomo sapiens (human)
alkaline phosphatase activityIntestinal-type alkaline phosphataseHomo sapiens (human)
protein bindingIntestinal-type alkaline phosphataseHomo sapiens (human)
zinc ion bindingIntestinal-type alkaline phosphataseHomo sapiens (human)
protein bindingPhospholipase A-2-activating proteinHomo sapiens (human)
phospholipase A2 activator activityPhospholipase A-2-activating proteinHomo sapiens (human)
ubiquitin bindingPhospholipase A-2-activating proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
mitochondrial intermembrane spaceAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
plasma membraneAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
mitochondrial membraneAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
extracellular regionAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
plasma membraneAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
membraneAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
extracellular matrixAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
extracellular exosomeAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
side of membraneAlkaline phosphatase, tissue-nonspecific isozymeHomo sapiens (human)
extracellular regionIntestinal-type alkaline phosphataseHomo sapiens (human)
plasma membraneIntestinal-type alkaline phosphataseHomo sapiens (human)
side of membraneIntestinal-type alkaline phosphataseHomo sapiens (human)
plasma membraneIntestinal-type alkaline phosphataseHomo sapiens (human)
nucleusPhospholipase A-2-activating proteinHomo sapiens (human)
cytoplasmPhospholipase A-2-activating proteinHomo sapiens (human)
synapsePhospholipase A-2-activating proteinHomo sapiens (human)
extracellular exosomePhospholipase A-2-activating proteinHomo sapiens (human)
cytoplasmPhospholipase A-2-activating proteinHomo sapiens (human)
nucleusPhospholipase A-2-activating proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID440273Inhibition of TNAP using DEA as substrate by non-competitive Lineweaver-Burke plot2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440268Cmax in rat at 4.13 mg/kg, sc2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440269Inhibition of TNAP right after mixing with enzyme (EI 0:0) by colorimetric assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440266Inhibition of NPP12009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440263Solubility at pH 7.4 by direct UV method2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID1372334Inhibition of TNAP (unknown origin) using PPi as substrate2018Bioorganic & medicinal chemistry letters, 01-01, Volume: 28, Issue:1
Discovery of 5-((5-chloro-2-methoxyphenyl)sulfonamido)nicotinamide (SBI-425), a potent and orally bioavailable tissue-nonspecific alkaline phosphatase (TNAP) inhibitor.
AID440271Inhibition of TNAP after 1 hr incubation with enzyme post-dilution (EI 1:0) by colorimetric assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440259Inhibition of TNAP transfected in african green monkey COS1 cells by colorimetric assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440261Metabolic stability in rat plasma after 30 mins2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440260Metabolic stability in rat liver microsomes after 30 mins2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID1372335Inhibition of TNAP (unknown origin) in whole blood using pNPP as substrate2018Bioorganic & medicinal chemistry letters, 01-01, Volume: 28, Issue:1
Discovery of 5-((5-chloro-2-methoxyphenyl)sulfonamido)nicotinamide (SBI-425), a potent and orally bioavailable tissue-nonspecific alkaline phosphatase (TNAP) inhibitor.
AID440264Inhibition of PLAP by luminescent assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440270Inhibition of TNAP after 1 hr pre-incubation with enzyme (EI 1:1) by colorimetric assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440267Inhibition of PHOSPHO1 assessed as inorganic phosphate release2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440272Inhibition of TNAP using CDP-star as substrate by non-competitive Lineweaver-Burke plot2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440262Permeability by PAMPA assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID440265Inhibition of IAP by luminescent assay2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Discovery and validation of a series of aryl sulfonamides as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (20.00)29.6817
2010's6 (60.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.00

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 Index12.00 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.00)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]