Page last updated: 2024-12-09

1-benzyl-2-phenylbenzimidazole

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Description

1-Benzyl-2-phenylbenzimidazole is a heterocyclic compound that contains a benzimidazole ring system.

**Structure:**

* It consists of a benzimidazole core, which is a five-membered ring containing two nitrogen atoms.
* A benzyl group (CH2-Ph) is attached to the nitrogen at the 1-position.
* A phenyl group (Ph) is attached to the carbon at the 2-position.

**Importance in Research:**

1-Benzyl-2-phenylbenzimidazole is of interest in research due to its potential **biological activities and applications**:

* **Anti-cancer activity:** Studies have shown that benzimidazole derivatives, including 1-benzyl-2-phenylbenzimidazole, exhibit anti-cancer properties. They can inhibit the growth and proliferation of various cancer cell lines.
* **Anti-microbial activity:** Benzimidazoles have been investigated for their potential as anti-bacterial, anti-fungal, and anti-viral agents. The specific activity of 1-benzyl-2-phenylbenzimidazole may depend on its structural modifications.
* **Ligand for metal complexes:** Benzimidazoles can act as ligands in coordination chemistry, forming complexes with various metal ions. These complexes may have applications in catalysis, materials science, and medicine.
* **Pharmacological studies:** 1-Benzyl-2-phenylbenzimidazole and related compounds are often synthesized and studied as potential drug candidates. Research focuses on identifying their pharmacokinetic and pharmacodynamic properties to evaluate their therapeutic potential.
* **Synthetic building blocks:** The benzimidazole ring system serves as a starting point for the synthesis of other biologically active molecules. This versatility makes it a valuable building block in medicinal chemistry.

**Note:** While research is ongoing, 1-benzyl-2-phenylbenzimidazole itself may not currently be used in any approved drugs or therapies.

It's important to remember that research on the biological activities of this compound is ongoing and the specific applications may still be under investigation.

1-benzyl-2-phenylbenzimidazole: has antineoplastic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1221687
CHEMBL ID1922082
SCHEMBL ID229828
MeSH IDM000609302

Synonyms (26)

Synonym
1-benzyl-2-phenyl-1h-benzimidazole
STL288023
CHEMDIV3_011388
1-benzyl-2-phenyl-1h-benzoimidazole
IDI1_028946
BRD-K09137815-001-01-9
HMS1505F14
AKOS000569392
1-benzyl-2-phenylbenzimidazole
1-benzyl-2-phenyl-1h-benzo[d]imidazole
739-88-8
2-phenyl-1-(phenylmethyl)-1h-benzimidazole
CHEMBL1922082
bdbm106769
1‐benzyl‐2‐phenyl‐1,3‐benzodiazole (b10)
4JV6
F0852-0127 ,
LCFXRSKBJWQHON-UHFFFAOYSA-N
SCHEMBL229828
1-benzyl-2-phenyl-1h-1,3-benzodiazole
DTXSID90361117
mfcd00844714
sr-01000417978
SR-01000417978-1
AS-36434
Q27451775
[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)
Xanthine dehydrogenase/oxidaseBos taurus (cattle)IC50 (µMol)9.70000.00303.10159.8000AID1800155
[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)
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)Kd1.82170.00110.84852.9000AID1154661; AID1154662; AID1455783
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
visual perceptionRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
GTPase inhibitor activityRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
protein bindingRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
small GTPase bindingRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine oxidase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
iron ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdenum ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
protein homodimerization activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
FAD bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
cytosolRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
cytoskeletonRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
ciliumRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
cytoplasmic vesicle membraneRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
cytoplasmic vesicleRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
cytoplasmRetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseBos taurus (cattle)
peroxisomeXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine dehydrogenase complexXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID631839Bactericidal activity against Bacillus cereus MTCC 430 assessed as log reduction in bacterial count at 0.2 mg/mL up to 48 hrs by time-kill assay2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1186340Antiviral activity against HSV1 infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 3 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID631841Bactericidal activity against Vibrio cholerae MTCC 3904 assessed as time required to complete extermination of bacteria at 0.2 mg/mL by time-kill assay2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1154661Binding affinity to PDE-delta (unknown origin) by time-resolved fluorescence anisotropic analysis2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Structure guided design and kinetic analysis of highly potent benzimidazole inhibitors targeting the PDEδ prenyl binding site.
AID631837Antibacterial activity against Bacillus cereus MTCC 430 assessed as zone of growth inhibition at 0.2 mg/ml after 18 to 24 hrs by Kirby-Bauer agar diffusion method2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1186328Antiviral activity against HIV1 infected in human MT4 cells assessed as inhibition of virus-induced cytopathogenicity after 4 days by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID631835Antibacterial activity against Vibrio cholerae MTCC 3904 assessed as zone of growth inhibition at 0.2 mg/ml after 18 to 24 hrs by Kirby-Bauer agar diffusion method2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1186334Cytotoxicity against mock-infected african green monkey Vero 76 cells after 48 to 96 hrs by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID631836Antibacterial activity against Escherichia coli MTCC 1610 assessed as zone of growth inhibition at 0.2 mg/ml after 18 to 24 hrs by Kirby-Bauer agar diffusion method2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1186327Cytotoxicity against mock-infected human MT4 cells after 96 hrs by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186338Antiviral activity against Vesicular stomatitis virus infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 2 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186336Antiviral activity against Poliovirus type 1 Sabin strain infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 2 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID631834Antibacterial activity against Staphylococcus aureus MTCC 3160 assessed as zone of growth inhibition at 0.2 mg/ml after 18 to 24 hrs by Kirby-Bauer agar diffusion method2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID631833Antibacterial activity against Shigella dysenteriae assessed as zone of growth inhibition at 0.2 mg/ml after 18 to 24 hrs by Kirby-Bauer agar diffusion method2011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.
AID1186330Antiviral activity against Bovine viral diarrhea virus infected in MDBK cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186342Selectivity index, ratio of CC50 for african green monkey Vero 76 cells to EC50 for Respiratory syncytial virus2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1231610Cytotoxicity against HUVEC assessed as inhibition of cell proliferation rate at 10 uM after 72 hrs by MTT assay relative to control2015Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID1231611Cytotoxicity against HUVEC assessed as inhibition of cell proliferation rate at 100 uM after 72 hrs by MTT assay relative to control2015Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.
AID1186333Antiviral activity against Reovirus type-1 infected in BHK21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186339Antiviral activity against Vaccinia Virus infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 3 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186332Antiviral activity against Yellow fever virus infected in BHK21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186329Cytotoxicity against mock-infected MDBK cells after 48 to 96 hrs by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1154662Binding affinity to PDE-delta (unknown origin) by SPR analysis2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Structure guided design and kinetic analysis of highly potent benzimidazole inhibitors targeting the PDEδ prenyl binding site.
AID1687307Antimicrobial activity against Escherichia coli JW55031 TolC mutant assessed as reduction in microbial growth incubated for 18 to 20 hrs by broth microdilution method2020European journal of medicinal chemistry, Jan-15, Volume: 186Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria.
AID1186335Antiviral activity against Coxsackievirus B5 infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 3 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186337Antiviral activity against Respiratory syncytial virus infected in african green monkey Vero 76 cells assessed as reduction in plaque number after 5 days by plaque reduction assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1186331Cytotoxicity against mock-infected BHK21 cells after 48 to 96 hrs by MTT assay2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.
AID1455783Inhibition of atorvastatin PEG-fluorescein binding to PDEdelta (unknown origin) by fluorescence polarization assay2018Journal of medicinal chemistry, 03-22, Volume: 61, Issue:6
Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design.
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.
AID1800155XO inhibitory activity from Article 10.1111/cbdd.12141: \\In vitro evaluation of selected benzimidazole derivatives as an antioxidant and xanthine oxidase inhibitors.\\2013Chemical biology & drug design, Sep, Volume: 82, Issue:3
In vitro evaluation of selected benzimidazole derivatives as an antioxidant and xanthine oxidase inhibitors.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2013Nature, May-30, Volume: 497, Issue:7451
Small molecule inhibition of the KRAS-PDEδ interaction impairs oncogenic KRAS signalling.
[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's0 (0.00)29.6817
2010's10 (90.91)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.21

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 Index13.21 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.70 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.21)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]