7467-35-8

Usage

Uses

Used in Pharmaceutical Industry:
(1-METHYL-1H-BENZOIMIDAZOL-2-YL)-METHANOL is used as a reagent for the synthesis of various benzimidazole-based compounds, which have been found to possess significant biological activities. These compounds are of interest in the development of new drugs, particularly in the treatment of various diseases and disorders.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1-METHYL-1H-BENZOIMIDAZOL-2-YL)-METHANOL is utilized in the design and synthesis of novel benzimidazole/indole-based PPARα and PPARβ partial agonists. These agonists are important targets for the treatment of metabolic diseases, such as diabetes and obesity, as well as other conditions like atherosclerosis and dyslipidemia.
Used in Antibacterial and Antifungal Applications:
(1-METHYL-1H-BENZOIMIDAZOL-2-YL)-METHANOL is also used in the development of benzimidazole-based compounds with antibacterial and antifungal properties. These compounds can be used as additives in the pharmaceutical, agricultural, and cosmetic industries to prevent the growth of harmful microorganisms and maintain product quality and safety.
Used in Structure-Activity Relationship Studies:
In addition to its applications in drug synthesis, (1-METHYL-1H-BENZOIMIDAZOL-2-YL)-METHANOL is employed in structure-activity relationship (SAR) studies. These studies involve the systematic investigation of the relationship between the chemical structure of a series of compounds and their biological activities. By understanding these relationships, researchers can design more effective and selective drugs with improved pharmacological properties.

InChI:InChI=1/C9H10N2O/c1-11-8-5-3-2-4-7(8)10-9(11)6-12/h2-5,12H,6H2,1H3

Upstream product

• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 1632-83-3 1-Methylbenzimidazole 
• 50-00-0 formaldehyd 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 35342-97-3 ethyl 1-methyl-1H-benzo[d]imidazole-2-carboxylate 
• 1865-09-4 ethyl 1H-benzimidazole-2-carboxylate 
• 74-83-9 methyl bromide 
• 79-14-1 glycolic Acid 
• 25148-68-9 N-methylbenzene-1,2-diamine dihydrochloride 
• 95-54-5 1,2-diamino-benzene 
• 64266-27-9 3-(2-Hydroxymethyl-benzoimidazol-1-yl)-propionitrile 

Downstream Products

• 14484-10-7 2-benzoyloxymethyl-1-methyl-1H-benzoimidazole 
• 4760-35-4 2-chloromethyl-1-methyl-1H-benzimidazole 
• 1357162-25-4 C₂₀H₁₈N₂O₃ 
• 1357162-33-4 C₂₀H₁₈N₂O₃ 
• 109029-13-2 4-[(1-methyl-1H-benzimidazol-2-yl)methoxy]aniline 
• 1413429-75-0 diethyl {4-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzylidene}propanedioate 
• 1413429-76-1 diethyl {4-[(1-methyl-1H-benzimidazol2-yl)methoxy]benzyl}propanedioate 
• 1413429-73-8 methyl 2-bromo-3-{4-[(1-methyl-1H-benzimidazol-2-yl)methoxy]phenyl}propanoate 
• 1413429-74-9 5-{4-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzylidene}-1,3-thiazolidine-2,4-dione 
• 118001-75-5 4-<(1-methyl-2-1H-benzimidazolyl)methoxy>benzaldehyde 
• 109029-43-8 C₁₅H₁₃N₃O₃ 
• 59871-40-8 2-benzyl-1-methyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

COMPOUNDS AS GLP-1R AGONISTS

The present application provides compounds that may be used as a glucagon-like peptide-1 receptors (GLP-1R) agonist, or stereoisomers, tautomers, or pharmaceutically acceptable salts of any of the foregoing. Also provided are pharmaceutical compositions containing such compounds, or stereoisomers, tautomers, or pharmaceutically acceptable salts of any of the foregoing. Methods of prepare these compounds and compositions and method of using them to treat or present a disease or a condition mediated by GLP-1R.

Design, synthesis, and antitumor activity of novel benzoheterocycle derivatives as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase

The vascular endothelial growth factor receptor-2 signaling pathway promotes the formation of new blood vessels, and vascular endothelial growth factor receptor-2 tyrosine kinase exists in both active and inactive conformations. Novel indole–benzimidazole and indole–benzothiazole derivatives joined by different linkers are designed and synthesized as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, HT29, A549, and MDA-MB-435) and human umbilical vein endothelial cell. Meanwhile, the inhibitory activities against vascular endothelial growth factor receptor-2 are estimated in vitro and the binding interactions with dual conformations of vascular endothelial growth factor receptor-2 tyrosine kinase are evaluated by molecular docking. Compounds 5a–c and 14 show inhibitory activity against vascular endothelial growth factor receptor-2 tyrosine kinase and promising cytotoxicity, specifically with IC50 values ranging between 0.1 and 1 μM, which imply broad-spectrum antitumor activity. These results provide a deep insight into potential structural modifications for developing potent vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.

ADENOSINE RECEPTOR BINDING COMPOUNDS

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

Kallikrein 5 inhibitors identified through structure based drug design in search for a treatment for Netherton Syndrome

Netherton syndrome (NS) is a rare and debilitating severe autosomal recessive genetic skin disease with high mortality rates particularly in neonates. NS is caused by loss-of-function SPINK5 mutations leading to unregulated kallikrein 5 (KLK5) and kallikrein 7 (KLK7) activity. Furthermore, KLK5 inhibition has been proposed as a potential therapeutic treatment for NS. Identification of potent and selective KLK5 inhibitors would enable further exploration of the disease biology and could ultimately lead to a treatment for NS. This publication describes how fragmentation of known trypsin-like serine protease (TLSP) inhibitors resulted in the identification of a series of phenolic amidine-based KLK5 inhibitors 1. X-ray crystallography was used to find alternatives to the phenol interaction leading to identification of carbonyl analogues such as lactam 13 and benzimidazole 15. These reversible inhibitors, with selectivity over KLK1 (10–100 fold), provided novel starting points for the guided growth towards suitable tool molecules for the exploration of KLK5 biology.

Cobalt(II) complexes based on (1-methyl-1H-benzo[d]imidazol-2-yl) methanol derivative: synthesis, crystal structure, spectroscopy, DFT calculations, and antioxidant activity

In this paper, we present a combined experimental and computational study of two new cobalt(II) complexes as [Co(Hmbm)2(OAc)2] and [Co(Hmbm)2(H2O)2]Cl2 (Hmbm = (1-methyl-1H-benzo[d]imidazol-2-yl)methanol). Both complexes were characterized by FT-IR and UV–vis spectroscopy, elemental analysis, and single-crystal X-ray crystallography. The molecular geometries, electronic transitions, and vibrational frequencies of the two complexes and the ligand (Hmbm) in the ground state have been calculated using global hybrid (B3LYP) and range-separated hybrid (CAM-B3LYP) density functional. Qualitative description of excited states and charge transfer character of electronic transitions states were carried out by plotting the Natural Transition Orbitals (NTOs) for main states, and were assigned to LMCT. The ligand and its Co(II) complexes have been evaluated for their potential as DPPH radical scavengers.

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi

A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.

Synthesis and biological evaluation of heterocyclic privileged medicinal structures containing (benz)imidazole unit

Abstract: New heterocyclic privileged medicinal scaffolds involving 4H-pyran, 1,4-dihydropyridine, quinazoline, and 2-aminochromene bearing a (benz)imidazole unit were prepared in good to excellent yields, and evaluated for their in vitro hepatotoxicity on HepG2 cells and antioxidant activity using DPPH radical-scavenging assay. From these results, 2-amino-4-(1-methyl-1H-imidazol-2-yl)-4H-benzo[h]chromene-3-carbonitrile has been identified as a racemic, readily available imidazole derivative, significantly less hepatotoxic than tacrine at 100?μM concentration. One compound was found to be a potent antioxidant agent. The catalytic effect of the 1-methylimidazole unit, in the synthesis of some heterocycle, was also demonstrated. Crystal X-ray structures are reported for six compounds. Graphical abstract: [Figure not available: see fulltext.]

Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives

(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.

New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies

A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50values of 3.26 ± 0.24 μM and 5.96 ± 0.67 μM respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells.

Synthesis and biological evaluation of new benzimidazole-thiazolidinedione hybrids as potential cytotoxic and apoptosis inducing agents

A series of new benzimidazole-thiazolidinedione hybrids has been synthesized and evaluated for their cytotoxic potential against a selected human cancer cell lines of prostate (PC-3 and DU-145), breast (MDA-MB-231), lung (A549) and a normal breast epithelial cells (MCF10A). Among the tested compounds, 11p exhibited promising cytotoxicity with IC50value of 11.46?±?1.46?μM on A549 lung cancer cell line and did not show significant toxicity on normal MCF10A cells. Lung cancer cells (A549) have been used to know the mechanism of cell growth inhibition and apoptosis inducing effect with compound 11p. The treatment of A549?cells with 11p showed typical apoptotic morphology like cell shrinkage, chromatin condensation and horseshoe shaped nuclei formation. Flow-cytometry analysis revealed the G2/M phase of cell cycle arrest in a dose dependent manner. Preliminary mechanistic studies suggested that the cell migration was inhibited through the disruption of F-actin protein. Acridine orange-ethidium bromide (AO-EB), DAPI, annexin V-FITC/propidium iodide, rhodamine-123 and MitoSOX assays suggested the induction of apoptosis in A549 cells by compound 11p.