Page last updated: 2024-12-09

1-[(3-methylphenyl)methyl]benzimidazole

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

1-[(3-methylphenyl)methyl]benzimidazole, often referred to as **1-(3-methylbenzyl)benzimidazole**, is a compound belonging to the benzimidazole family.

**Structure:**

* It consists of a benzimidazole core structure with a 3-methylbenzyl group (a benzyl group with a methyl substituent at the 3-position) attached at the N1 position.

**Importance in Research:**

1-[(3-methylphenyl)methyl]benzimidazole has shown potential in various research areas, primarily due to its pharmacological properties and potential applications in:

* **Anti-Cancer Activity:**
* Studies suggest that this compound exhibits anti-proliferative activity against various cancer cell lines, including leukemia, breast cancer, and colon cancer.
* It may target specific signaling pathways or proteins involved in cancer cell growth and survival.
* **Antimicrobial Activity:**
* Some research indicates that it possesses antibacterial and antifungal properties, potentially inhibiting the growth of pathogenic microorganisms.
* This area of research is still in its early stages, and further investigations are needed to understand its mechanism of action and efficacy.
* **Neuroprotective Effects:**
* Preliminary studies suggest that 1-(3-methylbenzyl)benzimidazole might possess neuroprotective properties, potentially protecting neurons from damage caused by oxidative stress or other insults.
* **Drug Delivery:**
* The benzimidazole core structure is often incorporated into drug delivery systems. This compound could potentially serve as a carrier for drug molecules, enhancing their bioavailability and targeting specific cells or tissues.

**Research Directions:**

* **Mechanism of Action:** Understanding the precise mechanisms by which 1-(3-methylbenzyl)benzimidazole exerts its biological effects is crucial for further development and potential therapeutic applications.
* **Structure-Activity Relationships:** Exploring the effect of modifying the structure of the compound on its pharmacological activities can lead to the design of more potent and specific derivatives.
* **Preclinical Studies:** Conducting in vivo studies in animal models is essential to assess the safety, efficacy, and potential therapeutic value of this compound.

**Note:** It's important to note that the research on 1-[(3-methylphenyl)methyl]benzimidazole is still ongoing, and the compound is not currently approved for any clinical use.

Cross-References

ID SourceID
PubMed CID886929
CHEMBL ID1450329
CHEBI ID115498
SCHEMBL ID14817163

Synonyms (23)

Synonym
STL290623
bdbm50335362
smr000142443
MLS000535007
1-(3-methylbenzyl)-1h-benzimidazole
IFLAB1_005093
1-(3-methyl-benzyl)-1h-benzoimidazole
CHEBI:115498
AKOS000587141
HMS1426H11
1-[(3-methylphenyl)methyl]benzimidazole
CHEMBL1450329 ,
HMS2332A06
1-(3-methylbenzyl)-1h-benzo[d]imidazole
537018-04-5
F1221-0022
SCHEMBL14817163
Q27197351
sr-01000252871
SR-01000252871-1
1-[(3-methylphenyl)methyl]-1h-1,3-benzodiazole
Z54664766
EN300-13909603
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzimidazolesAn organic heterocyclic compound containing a benzene ring fused to an imidazole 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 (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency39.81075.623417.292931.6228AID485281
ATAD5 protein, partialHomo sapiens (human)Potency32.64270.004110.890331.5287AID504467
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency4.46683.548119.542744.6684AID743266
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency79.43280.050127.073689.1251AID588590
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency7.94330.00798.23321,122.0200AID2551
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency31.62280.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency31.62280.00638.235039.8107AID881
Guanine nucleotide-binding protein GHomo sapiens (human)Potency8.15481.995325.532750.1187AID624287; AID624288
[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)
Cytochrome P450 11B1, mitochondrialHomo sapiens (human)IC50 (µMol)0.19400.00050.29022.7800AID553065
Cytochrome P450 11B2, mitochondrialHomo sapiens (human)IC50 (µMol)0.30900.00010.27383.5000AID553066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
C21-steroid hormone biosynthetic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
glucocorticoid biosynthetic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
immune responseCytochrome P450 11B1, mitochondrialHomo sapiens (human)
regulation of blood pressureCytochrome P450 11B1, mitochondrialHomo sapiens (human)
sterol metabolic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
aldosterone biosynthetic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cellular response to hormone stimulusCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cortisol biosynthetic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cellular response to potassium ionCytochrome P450 11B1, mitochondrialHomo sapiens (human)
glucose homeostasisCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cholesterol metabolic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cortisol metabolic processCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cellular response to peptide hormone stimulusCytochrome P450 11B1, mitochondrialHomo sapiens (human)
cortisol biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
regulation of blood volume by renal aldosteroneCytochrome P450 11B2, mitochondrialHomo sapiens (human)
renal water homeostasisCytochrome P450 11B2, mitochondrialHomo sapiens (human)
C21-steroid hormone biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
mineralocorticoid biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
sterol metabolic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
aldosterone biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cellular response to hormone stimulusCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cortisol biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cellular response to potassium ionCytochrome P450 11B2, mitochondrialHomo sapiens (human)
potassium ion homeostasisCytochrome P450 11B2, mitochondrialHomo sapiens (human)
sodium ion homeostasisCytochrome P450 11B2, mitochondrialHomo sapiens (human)
glucocorticoid biosynthetic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cortisol metabolic processCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cellular response to peptide hormone stimulusCytochrome P450 11B2, mitochondrialHomo sapiens (human)
cholesterol metabolic processCytochrome P450 11B2, mitochondrialHomo 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 (14)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
steroid 11-beta-monooxygenase activityCytochrome P450 11B1, mitochondrialHomo sapiens (human)
iron ion bindingCytochrome P450 11B1, mitochondrialHomo sapiens (human)
heme bindingCytochrome P450 11B1, mitochondrialHomo sapiens (human)
corticosterone 18-monooxygenase activityCytochrome P450 11B1, mitochondrialHomo sapiens (human)
steroid 11-beta-monooxygenase activityCytochrome P450 11B2, mitochondrialHomo sapiens (human)
iron ion bindingCytochrome P450 11B2, mitochondrialHomo sapiens (human)
steroid hydroxylase activityCytochrome P450 11B2, mitochondrialHomo sapiens (human)
heme bindingCytochrome P450 11B2, mitochondrialHomo sapiens (human)
corticosterone 18-monooxygenase activityCytochrome P450 11B2, mitochondrialHomo 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 (10)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
mitochondrionCytochrome P450 11B1, mitochondrialHomo sapiens (human)
mitochondrial inner membraneCytochrome P450 11B1, mitochondrialHomo sapiens (human)
mitochondrial inner membraneCytochrome P450 11B1, mitochondrialHomo sapiens (human)
mitochondrionCytochrome P450 11B2, mitochondrialHomo sapiens (human)
mitochondrial inner membraneCytochrome P450 11B2, mitochondrialHomo sapiens (human)
mitochondrial inner membraneCytochrome P450 11B2, mitochondrialHomo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary 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.
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.
AID553069Inhibition of human placental microsomes CYP19 at 500 nM using androstenedione substrate2011ACS medicinal chemistry letters, Jan-13, Volume: 2, Issue:1
First Selective CYP11B1 Inhibitors for the Treatment of Cortisol-Dependent Diseases.
AID553066Inhibition of human CYP11B2 expressed in hamster V79MZ cells using 11-deoxycorticosterone substrate2011ACS medicinal chemistry letters, Jan-13, Volume: 2, Issue:1
First Selective CYP11B1 Inhibitors for the Treatment of Cortisol-Dependent Diseases.
AID553067Selectivity index, ratio of IC50 for human CYP11B2 to IC50 for human CYP11B12011ACS medicinal chemistry letters, Jan-13, Volume: 2, Issue:1
First Selective CYP11B1 Inhibitors for the Treatment of Cortisol-Dependent Diseases.
AID553065Inhibition of human CYP11B1 expressed in hamster V79MZ cells using 11-deoxycorticosterone substrate2011ACS medicinal chemistry letters, Jan-13, Volume: 2, Issue:1
First Selective CYP11B1 Inhibitors for the Treatment of Cortisol-Dependent Diseases.
AID553068Inhibition of human recombinant CYP17 expressed in Escherichia coli at 2 uM using progesterone substrate2011ACS medicinal chemistry letters, Jan-13, Volume: 2, Issue:1
First Selective CYP11B1 Inhibitors for the Treatment of Cortisol-Dependent Diseases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's4 (66.67)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.35

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 Index12.35 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.35)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]