Page last updated: 2024-12-06

5-Methoxyisatin

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

5-Methoxyisatin is a derivative of isatin, a heterocyclic compound with a wide range of biological activities. It has been investigated for its potential applications in various fields, including:

- **Antioxidant properties:** 5-Methoxyisatin exhibits antioxidant activity, which has been linked to its ability to scavenge free radicals.
- **Anti-cancer activity:** Studies have shown that 5-Methoxyisatin has anti-proliferative effects on certain cancer cell lines.
- **Anti-inflammatory activity:** It has been demonstrated that 5-Methoxyisatin possesses anti-inflammatory properties, potentially through modulation of inflammatory pathways.
- **Neuroprotective effects:** Some research suggests that 5-Methoxyisatin may provide neuroprotection against oxidative stress and neurotoxicity.

The synthesis of 5-Methoxyisatin involves various methods, including:

- **Fischer indole synthesis:** This classic method utilizes phenylhydrazine and a suitable ketone or aldehyde to generate the indole ring system.
- **Modified Fischer indole synthesis:** Variations of the Fischer indole synthesis have been developed to optimize the synthesis of 5-Methoxyisatin.

Due to its diverse biological activities and potential therapeutic applications, 5-Methoxyisatin is a subject of ongoing research in the fields of medicine, chemistry, and pharmacology.'

Cross-References

ID SourceID
PubMed CID38333
CHEMBL ID222660
CHEBI ID149863
SCHEMBL ID21602

Synonyms (54)

Synonym
39755-95-8
nsc-88052
nsc88052
BB 0254516
brn 0139520
1h-indole-2,3-dione, 5-methoxy-
indole-2,3-dione, 5-methoxy-
nsc 88052
5-methoxy-indole-2,3-dione
bdbm22811
isatin-based compound, 31
5-methoxy-2,3-dihydro-1h-indole-2,3-dione
MLS000561694
smr000177846
5-methoxy-1h-indole-2,3-dione
EC-000.1696
5-methoxyisatin
STK215331
AKOS000200895
CHEMBL222660
F0896-0193
5-methoxy-2,3-indolinedione ,
5-methoxyindole-2,3-dione
M1362
CHEBI:149863
A20428
NCGC00245347-01
HMS2557P21
5-methoxyindoline-2,3-dione
MLS002473346
c7ga9u9tn1 ,
5-21-13-00116 (beilstein handbook reference)
unii-c7ga9u9tn1
FT-0639576
FS-2332
CL3515
SCHEMBL21602
MB00814
mfcd00169023
SY021560
5-methoxy isatin
5-methoxyisatine
5-methoxy-1h-indole-2,3-dione #
AC-28109
J-517701
1h-indole-2,3-dione, 5-methoxy- (9ci)
DTXSID00192838
sr-01000390541
SR-01000390541-1
CS-W001176
isatin, 5-methoxy-
EN300-17177
AMY3503
Z56899037
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
anticoronaviral agentAny antiviral agent which inhibits the activity of coronaviruses.
[role 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]

Drug Classes (1)

ClassDescription
indolesAny compound containing an indole skeleton.
[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 (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency44.66840.044717.8581100.0000AID485294
ATAD5 protein, partialHomo sapiens (human)Potency25.92900.004110.890331.5287AID504467
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency89.12510.707936.904389.1251AID504333
DNA polymerase eta isoform 1Homo sapiens (human)Potency17.78280.100028.9256213.3130AID588591
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
[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)
Coagulation factor XIIHomo sapiens (human)Ki85.34000.00251.86697.2500AID1798240
CholinesteraseHomo sapiens (human)Ki87.78330.00001.51739.7300AID1798240; AID281481
Liver carboxylesterase 1Oryctolagus cuniculus (rabbit)Ki85.34000.01361.70257.2500AID1798240
AcetylcholinesteraseHomo sapiens (human)Ki87.78330.00001.27869.7300AID1798240; AID281480
Liver carboxylesterase 1Homo sapiens (human)Ki87.78330.00252.01368.4800AID1798240; AID281478
[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)
glycogen synthase kinase-3 beta isoform 1Homo sapiens (human)EC50 (µMol)300.00000.212522.156283.9400AID434954
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (54)

Processvia Protein(s)Taxonomy
plasma kallikrein-kinin cascadeCoagulation factor XIIHomo sapiens (human)
Factor XII activationCoagulation factor XIIHomo sapiens (human)
blood coagulation, intrinsic pathwayCoagulation factor XIIHomo sapiens (human)
positive regulation of plasminogen activationCoagulation factor XIIHomo sapiens (human)
protein processingCoagulation factor XIIHomo sapiens (human)
protein autoprocessingCoagulation factor XIIHomo sapiens (human)
positive regulation of blood coagulationCoagulation factor XIIHomo sapiens (human)
zymogen activationCoagulation factor XIIHomo sapiens (human)
fibrinolysisCoagulation factor XIIHomo sapiens (human)
innate immune responseCoagulation factor XIIHomo sapiens (human)
response to misfolded proteinCoagulation factor XIIHomo sapiens (human)
positive regulation of fibrinolysisCoagulation factor XIIHomo sapiens (human)
blood coagulationCoagulation factor XIIHomo sapiens (human)
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)
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityCoagulation factor XIIHomo sapiens (human)
calcium ion bindingCoagulation factor XIIHomo sapiens (human)
protein bindingCoagulation factor XIIHomo sapiens (human)
misfolded protein bindingCoagulation factor XIIHomo sapiens (human)
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)
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
extracellular regionCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
plasma membraneCoagulation factor XIIHomo sapiens (human)
collagen-containing extracellular matrixCoagulation factor XIIHomo sapiens (human)
extracellular exosomeCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
rough endoplasmic reticulumCoagulation factor XIIHomo sapiens (human)
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)
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1798240Enzyme Inhibition Assay from Article 10.1021/jm061471k: \\Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.\\2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
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.
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.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1063516Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID281479Inhibition of rabbit liver carboxylesterase expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1082385Inhibition of Arabidopsis thaliana AHAS at 100 mg/L colorimetric assay2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1063518Cytotoxicity against human K562 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID284490Cytotoxicity against human U937 cells2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
In vitro cytotoxicity evaluation of some substituted isatin derivatives.
AID1063517Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID1061202Inhibition of GST-tagged SARS coronavirus 3C-like protease at 1 mM by FRET assay2014Bioorganic & medicinal chemistry, Jan-01, Volume: 22, Issue:1
Synthesis, modification and docking studies of 5-sulfonyl isatin derivatives as SARS-CoV 3C-like protease inhibitors.
AID281477Inhibition of human intestinal carboxylesterase expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1082383Inhibition of Brassica rapa subsp. oleifera root growth at 10 mg/L2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1082384Inhibition of Brassica rapa subsp. oleifera at 100 mg/L2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1284106Anticancer activity against human Jurkat cells after 48 hrs by MTT assay2016European journal of medicinal chemistry, Apr-13, Volume: 112Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives.
AID281480Inhibition of human AChE2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1406678Antiproliferative activity against human K562 cells after 48 hrs by MTT assay
AID465619Anticancer activity against human U937 cells by MTS assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
QSAR study of isatin analogues as in vitro anti-cancer agents.
AID281478Inhibition of human liver CE1 expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1406679Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay
AID281481Inhibition of human BChE2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (23.08)29.6817
2010's9 (69.23)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.39

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.39 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.39)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]