68426-72-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole-2-methanol,1,5-dimethyl-(9CI) is used as a building block in the synthesis of various pharmaceuticals due to its diverse biological activities. It exhibits potential antiparasitic, antifungal, and antibacterial properties, making it a valuable component for the development of new drugs.
Used in Agrochemical Industry:
1H-Benzimidazole-2-methanol,1,5-dimethyl-(9CI) is also used in the synthesis of agrochemicals, contributing to its potential applications in agriculture. Its antiparasitic, antifungal, and antibacterial properties can be harnessed to develop new agrochemicals for crop protection and disease management.
Used in Antitumor and Anti-inflammatory Research:
1H-Benzimidazole-2-methanol,1,5-dimethyl-(9CI) has been studied for its potential as an antitumor and anti-inflammatory agent. Its biological activities and molecular structure make it a promising candidate for further research and development in these therapeutic areas.

InChI:InChI=1/C10H12N2O/c1-7-3-4-9-8(5-7)11-10(6-13)12(9)2/h3-5,13H,6H2,1-2H3

Upstream product

• 20034-02-0 (5-methyl-1H-benzimidazole-2-yl)methanol 
• 74-88-4 methyl iodide 
• 496-72-0 4-methyl-1,2-diaminobenzene 

Downstream Products

• 1357162-26-5 C₂₁H₂₀N₂O₃ 
• 1357162-35-6 C₂₁H₂₀N₂O₃ 
• 37735-10-7 1,5-dimethyl-1H-benzoimidazole-2-carbaldehyde 
• 68426-73-3 2-chloromethyl-1,5-dimethyl-1H-benzoimidazole 

Relevant academic research and scientific papers

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 evaluation of selected benzimidazole derivatives as potential antimicrobial agents

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity

A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4- methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 μM has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 μM has a strong inhibitory effect on the growth of MCF-7 cancer cells.