Page last updated: 2024-11-05

2-(2'-hydroxyphenyl)benzimidazole

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Description

2-(2'-hydroxyphenyl)benzimidazole is a benzimidazole derivative with a hydroxyl group at the ortho position of the phenyl ring. It has been reported to exhibit a range of biological activities, including anti-inflammatory, antioxidant, and anticancer effects. Research suggests that the compound may exert its effects through various mechanisms, such as inhibiting the production of pro-inflammatory cytokines, scavenging reactive oxygen species, and inducing apoptosis in cancer cells. Its potential therapeutic applications have led to ongoing research efforts to explore its efficacy and safety in treating inflammatory diseases, oxidative stress-related conditions, and cancer. The compound's unique structural features, including the presence of both benzimidazole and hydroxyl groups, are believed to contribute to its diverse biological activities. Synthesis of the compound often involves reactions like the condensation of o-phenylenediamine with a suitable salicylaldehyde derivative.'

2-(2'-hydroxyphenyl)benzimidazole: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID18075
CHEMBL ID203360
SCHEMBL ID461968
MeSH IDM0589927

Synonyms (52)

Synonym
STK726803
BB 0219527
phenol, o-2-benzimidazolyl-
nsc-32819
nsc32819
phenol, 2-(1h-benzimidazol-2-yl)-
2-(2'-oxyphenyl)benzimidazole
2-(o-hydroxyphenyl)benzimidazole
2-(2-hydroxyphenyl)benzimidazole
2-(2'-hydroxyphenyl)benzimidazole
2-(2-benzimidazolyl)phenol
2963-66-8
DIVK1C_003471
CDS1_002431
OPREA1_643153
2-(1h-benzoimidazol-2-yl)-phenol
OPREA1_407005
CHEMDIV1_018687
2-(2-hydroxyphenyl)-1h-benzimidazole, 95%
AKOS000275527
CHEMBL203360 ,
HMS640B09
2-(1h-benzo[d]imidazol-2-yl)phenol
2-(1h-benzimidazol-2-yl)phenol
bdbm50180727
6-(1,3-dihydrobenzimidazol-2-ylidene)cyclohexa-2,4-dien-1-one
2-(2-hydroxyphenyl)-1h-benzimidazole
nsc 32819
CCG-15084
2-(2-hydroxyphenyl)-1h-benzoimidazole
2-(1h-benzimidazole-2-yl)phenol
2-(1h-benzimidazole-z-yl)phenol
F0852-0136
H1736
DTXSID7062746
mfcd00022668
SCHEMBL461968
2-(2-hydroxyphenyl)1h-benzimidazole
cambridge id 5310716
2-(1h-1,3-benzodiazol-2-yl)phenol
phenol,2-(1h-benzimidazol-2-yl)-
sr-01000389041
SR-01000389041-1
J-017586
CS-0196394
2-(2 inverted exclamation marka-hydroxyphenyl)benzimidazole
AS-37909
AMY27157
HY-W140203
CAA96366
PD158855
Z57115066
[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)
Methionine aminopeptidaseEscherichia coli K-12IC50 (µMol)10.00000.47203.50775.0000AID259066
Fatty-acid amide hydrolase 1Rattus norvegicus (Norway rat)IC50 (µMol)10.00000.00051.33138.0000AID259066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
proteolysisMethionine aminopeptidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
aminopeptidase activityMethionine aminopeptidaseEscherichia coli K-12
initiator methionyl aminopeptidase activityMethionine aminopeptidaseEscherichia coli K-12
ferrous iron bindingMethionine aminopeptidaseEscherichia coli K-12
metalloexopeptidase activityMethionine aminopeptidaseEscherichia coli K-12
metal ion bindingMethionine aminopeptidaseEscherichia coli K-12
metalloaminopeptidase activityMethionine aminopeptidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolMethionine aminopeptidaseEscherichia coli K-12
cytosolMethionine aminopeptidaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID489475Inhibition of human MetAP2 expressed in baculovirus infected Sf9 cells at 25 uM2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors.
AID1440295Inhibition of full length recombinant human His-tagged IDO1 expressed in mouse LLTC cells using L-tryptophan as substrate after 24 hrs2017European journal of medicinal chemistry, Jan-27, Volume: 126Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.
AID755683Antioxidant activity assessed as superoxide radical anion scavenging activity by spectrophotometric analysis2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1382573Inhibition of electric eel AChE using acetylthiocholine iodide as substrate preincubated for 15 mins followed by addition of substrate measured after 5 mins2018European journal of medicinal chemistry, Mar-25, Volume: 148Novel Tacrine-Hydroxyphenylbenzimidazole hybrids as potential multitarget drug candidates for Alzheimer's disease.
AID755682Antioxidant activity assessed as hydroxyl radical scavenging activity after 1 hr by spectrophotometric analysis2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1382574Antioxidant activity assessed as DPPH radical scavenging activity incubated for 30 mins2018European journal of medicinal chemistry, Mar-25, Volume: 148Novel Tacrine-Hydroxyphenylbenzimidazole hybrids as potential multitarget drug candidates for Alzheimer's disease.
AID259066Inhibition of Co2+ loaded MetAP expressed in Escherichia coli2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Metal-mediated inhibition of Escherichia coli methionine aminopeptidase: structure-activity relationships and development of a novel scoring function for metal-ligand interactions.
AID259067Inhibition of Mn2+ loaded MetAP expressed in Escherichia coli at upto 10 uM2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Metal-mediated inhibition of Escherichia coli methionine aminopeptidase: structure-activity relationships and development of a novel scoring function for metal-ligand interactions.
AID269392Potency index, spasmolytic activity in Wistar rat ileum relative to gigantol2006Bioorganic & medicinal chemistry letters, Aug-15, Volume: 16, Issue:16
Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres.
AID755674Antibacterial activity against Escherichia coli after 24 hrs by agar dilution method2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1917873Antiproliferative activity against human U-251MG cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Recent Scaffold Hopping Applications in Central Nervous System Drug Discovery.
AID269391Spasmolytic activity in Wistar rat ileum2006Bioorganic & medicinal chemistry letters, Aug-15, Volume: 16, Issue:16
Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres.
AID1917875Antiproliferative activity against human IN1760 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Recent Scaffold Hopping Applications in Central Nervous System Drug Discovery.
AID1571462Antiproliferative activity against human IN1528 cells after 72 hrs by sulforhodamine B assay2018MedChemComm, Nov-01, Volume: 9, Issue:11
Towards identifying potent new hits for glioblastoma.
AID1440277Inhibition of recombinant human IDO1 expressed in bacterial expression system at 400 uM using L-Tryptophan as substrate after 25 mins by fluorescence assay relative to control2017European journal of medicinal chemistry, Jan-27, Volume: 126Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.
AID489471Inhibition of Staphylococcus aureus MetAP at 25 uM2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors.
AID755670Antibacterial activity against Bacillus cereus after 24 hrs by agar dilution method2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID419582Inhibition of calf thymus DNA topoisomerase 1-mediated relaxation of supercoiled pBR322 plasmid DNA at 1 ug/ml by agarose gel electrophoresis2009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays.
AID1440271Inhibition of recombinant human IDO1 S167A mutant expressed in Escherichia coli SG13009(pREP4) using L-Tryptophan as substrate after 25 mins by fluorescence assay2017European journal of medicinal chemistry, Jan-27, Volume: 126Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.
AID755671Antibacterial activity against Staphylococcus albus after 24 hrs by agar dilution method2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1917874Antiproliferative activity against human IN1528 cells assessed as inhibition of cell growth incubated for 72 hrs by SRB assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Recent Scaffold Hopping Applications in Central Nervous System Drug Discovery.
AID1571463Antiproliferative activity against human IN1760 cells after 72 hrs by sulforhodamine B assay2018MedChemComm, Nov-01, Volume: 9, Issue:11
Towards identifying potent new hits for glioblastoma.
AID755673Antibacterial activity against Pseudomonas aeruginosa after 24 hrs by agar dilution method2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1571459Antiproliferative activity against human U87MG cells after 72 hrs by sulforhodamine B assay2018MedChemComm, Nov-01, Volume: 9, Issue:11
Towards identifying potent new hits for glioblastoma.
AID1571460Antiproliferative activity against human U251MG cells after 72 hrs by sulforhodamine B assay2018MedChemComm, Nov-01, Volume: 9, Issue:11
Towards identifying potent new hits for glioblastoma.
AID755672Antibacterial activity against Staphylococcus aureus after 24 hrs by agar dilution method2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID259068Inhibition of Co2+ loaded MetAP expressed in Escherichia coli at 10 uM2006Journal of medicinal chemistry, Jan-26, Volume: 49, Issue:2
Metal-mediated inhibition of Escherichia coli methionine aminopeptidase: structure-activity relationships and development of a novel scoring function for metal-ligand interactions.
AID489469Inhibition of Escherichia coli MetAP at 25 uM2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors.
AID489473Inhibition of human MetAP1 at 25 uM2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
Subtype-selectivity of metal-dependent methionine aminopeptidase inhibitors.
AID419581Inhibition of calf thymus DNA topoisomerase 1-mediated relaxation of supercoiled pBR322 plasmid DNA by agarose gel electrophoresis2009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays.
AID419584Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays.
AID419583Cytotoxicity against human A431 cells after 72 hrs by MTT assay2009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays.
AID755681Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by spectrophotometric analysis2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID419585Cytotoxicity against human MCF7 cells after 72 hrs by MTT assay2009European journal of medicinal chemistry, May, Volume: 44, Issue:5
Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays.
AID1440296Cytotoxicity against mouse LLTC cells assessed as reduction in cell viability after 24 hrs by MTT assay2017European journal of medicinal chemistry, Jan-27, Volume: 126Discovery and evaluation of inhibitors to the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1 (IDO1): Probing the active site-inhibitor interactions.
AID755669Cytotoxicity against mouse NIH/3T3 cells after 48 hrs by SRB assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives.
AID1571461Antiproliferative activity against human IN1472 cells after 72 hrs by sulforhodamine B assay2018MedChemComm, Nov-01, Volume: 9, Issue:11
Towards identifying potent new hits for glioblastoma.
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).
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (18.75)29.6817
2010's11 (68.75)24.3611
2020's2 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.02

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 Index12.02 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]