Page last updated: 2024-11-05

2-hydroxybenzothiazole

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

Description

2-Hydroxybenzothiazole, also known as o-hydroxybenzothiazole, is a heterocyclic compound with a wide range of applications. Its synthesis typically involves the reaction of o-aminophenol with carbon disulfide in the presence of a base. 2-Hydroxybenzothiazole exhibits various biological activities, including antimicrobial, antifungal, and antioxidant properties. It is also used as an intermediate in the synthesis of dyes and pharmaceuticals. Research on 2-Hydroxybenzothiazole is driven by its potential in various fields, including medicine, agriculture, and materials science. Its unique structure and properties make it a valuable building block for the development of novel compounds with desirable functionalities.'

2-hydroxybenzothiazole : Benzothiazole substituted with a hydroxy group at the 2-position. [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]

Cross-References

ID SourceID
PubMed CID13625
CHEMBL ID276936
CHEBI ID115196
SCHEMBL ID54329

Synonyms (93)

Synonym
benzothiazolol
nsc-7706
nsc7706
carbamothioic acid, .gamma.-lactone
benzothiazolone
2-benzothiazolinone
2-benzothiazolone
2(3h)-benzothiazolone
2-benzothiazolol
2-hydroxybenzothiazole
934-34-9
mls000737673 ,
nsc-26422
nsc-33823
nsc26422
nsc33823
smr000112468
MLS000697050
OBT ,
s-orthophenylenethiocarbamate
1,3-benzothiazol-2-ol
STK089714
1,3-benzothiazol-2(3h)-one
benzthiazoline,2-one
inchi=1/c7h5nos/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4h,(h,8,9
SR-01000640954-1
2-hydroxybenzothiazole, 98%
nsc 7706
(2-mercatophenyl)carbamothioic acid gamma-lactone
2-hydroxy-1,3-benzothiazole
CHEBI:115196 ,
b2344 ,
3h-benzothiazol-2-one
AKOS000296755
HMS1661I01
3h-1,3-benzothiazol-2-one
CHEMBL276936
F0918-5160
STK894866
AKOS000638434
HMS1652A15
EN300-88615
2,3-dihydro-1,3-benzothiazol-2-one
benzo[d]thiazol-2(3h)-one ,
A19331
NCGC00246613-01
NCGC00246794-01
einecs 213-281-1
unii-7t26k7ng46
7t26k7ng46 ,
carbamothioic acid, (2-mercatophenyl)-, gamma-lactone
ai3-24484
nsc 33823
nsc 26422
HMS2269D03
CCG-51664
benzo[d]thiazol-2-ol
GEO-01505
AE-018/31855052
74343-69-4
FT-0612585
FS-3774
benzothiazol-2-ol
cid_13625
bdbm93696
EPITOPE ID:138948
3h-benzothiazole-2-one
2-oxobenzothiazole
SCHEMBL54329
benzothiazolin-2-one
hydroxybenzothiazole
2-hydroxy-benzothiazole
benzthiazolin-2-one
hydroxybenzothiazol
FS-1222
SY003005
mfcd00022868
DTXSID6061315
2-benzothiazolol (keto form)
1,3-benzothiazol-2(3h)-one #
benzothiazol, 2-hydroxy-
carbamothioic acid, (2-mercatophenyl)-, .gamma.-lactone
W-200528
J-640182
STR06157
Q27197041
J-800183
Z57728688
CS-W019496
2-oh-bth
F14867
AMY15529
CGD ,
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzothiazoleAn organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.31620.044717.8581100.0000AID485294
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.77830.035520.977089.1251AID504332
Rap guanine nucleotide exchange factor 3Homo sapiens (human)Potency89.12516.309660.2008112.2020AID720709
Guanine nucleotide-binding protein GHomo sapiens (human)Potency11.22021.995325.532750.1187AID624287
[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)
sentrin-specific protease 8Homo sapiens (human)IC50 (µMol)100.00000.040818.929294.8000AID624322; AID651559
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
adaptive immune responseRap guanine nucleotide exchange factor 3Homo sapiens (human)
signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 3Homo sapiens (human)
associative learningRap guanine nucleotide exchange factor 3Homo sapiens (human)
Rap protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of actin cytoskeleton organizationRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
intracellular signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of GTPase activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of protein export from nucleusRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of stress fiber assemblyRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
establishment of endothelial barrierRap guanine nucleotide exchange factor 3Homo sapiens (human)
cellular response to cAMPRap guanine nucleotide exchange factor 3Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein domain specific bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
cortical actin cytoskeletonRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
microvillusRap guanine nucleotide exchange factor 3Homo sapiens (human)
endomembrane systemRap guanine nucleotide exchange factor 3Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
lamellipodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
filopodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
extracellular exosomeRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID394498Inhibition of Escherichia coli recombinant DNA gyrase-mediated supercoiling of relaxed pRSET A-DNA by agarose gel electrophoresis2007Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10
Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening.
AID137583The compound was tested for neurologic toxicity (rotarod) test for 30 min in mice; active at 100 mg/kg1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
AID137584The compound was tested for neurologic toxicity (rotarod) test for 4 hours in mice; active at 300 mg/kg1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
AID1059430Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 using L-tryptophan as substrate at 1 mM after 1 hr relative to control2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Discovery and characterisation of hydrazines as inhibitors of the immune suppressive enzyme, indoleamine 2,3-dioxygenase 1 (IDO1).
AID133130The compound was tested for anticonvulsant activity in Maximal electroshock seizure test (MES) for 4 hr in mice(ip); active at 300 mg/kg1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
AID1893771Inhibition of recombinant human QC using H-Gln-AMC hydrobromide as fluorogenic substrate incubated for 6 hrs by fluorometric microplate reader analysis2022ACS medicinal chemistry letters, Sep-08, Volume: 13, Issue:9
2-Amino-1,3,4-thiadiazoles as Glutaminyl Cyclases Inhibitors Increase Phagocytosis through Modification of CD47-SIRPĪ± Checkpoint.
AID133132Anticonvulsant activity in Maximal electroshock seizure test at 100 mg/kg i.p. in mice.1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
AID140597The compound was tested for anticonvulsant activity in subcutaneous pentylenetetrazole seizure test (sc Met) for 30 min in mice; active at 100 mg/kg1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
AID140602The compound was tested for anticonvulsant activity in subcutaneous pentylenetetrazole seizure test (sc Met) for 4 hr in mice; active at 300 mg/kg1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives.
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 (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.14)18.2507
2000's2 (14.29)29.6817
2010's8 (57.14)24.3611
2020's3 (21.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.10

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 Index29.10 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index28.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.10)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]