6646-70-4

Usage

Uses

Used in Pharmaceutical Industry:
(1-Benzyl-1H-benzimidazol-2-yl)methanol is utilized as a key intermediate in the synthesis of various pharmaceuticals due to its unique molecular structure and potential biological activities. Its antiviral, antimicrobial, and anticancer properties make it a valuable component in the development of new drugs targeting a range of diseases and conditions.
Used in Bioactive Compounds Synthesis:
In the field of medicinal chemistry, (1-benzyl-1H-benzimidazol-2-yl)methanol is employed as a precursor for the synthesis of bioactive compounds, leveraging its chemical properties to create molecules with therapeutic potential.
Used in Drug Discovery:
(1-Benzyl-1H-benzimidazol-2-yl)methanol is used as a starting material in drug discovery processes, where its potential biological activities are harnessed to identify and develop new therapeutic agents.
Used in Materials Science:
In the materials science industry, (1-benzyl-1H-benzimidazol-2-yl)methanol is used as a component in the research and development of novel polymers and functional materials, capitalizing on its chemical structure to create innovative materials with unique properties.

InChI:InChI=1/C15H14N2O/c18-11-15-16-13-8-4-5-9-14(13)17(15)10-12-6-2-1-3-7-12/h1-9,18H,10-11H2

Upstream product

• 944061-83-0 C₁₇H₁₆N₂O₂ 
• 33809-91-5 (1H-benzo[d]imidazol-2-yl)methyl acetate 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 141-46-8 Glycolaldehyde 
• 100-39-0 benzyl bromide 
• 5822-13-9 N-benzyl-1,2-phenylenediamine 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 95-54-5 1,2-diamino-benzene 
• 100-44-7 benzyl chloride 
• 449796-13-8 N-acetoxy-2-(acetoxymethyl)benzimidazole 

Downstream Products

• 180000-91-3 1-benzyl-1H-benzo[d]imidazole-2-carbaldehyde 
• 189560-87-0 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazine-1-carbaldehyde 
• 7192-00-9 1-benzyl-2-(chloromethyl)-1H-benzo[d]imidazole 
• 1568975-31-4 benzyl 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazine-1-carboxylate 
• 1211330-70-9 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)-N-phenylpiperazine-1-carboxamide 
• 1172525-83-5 (4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)(phenyl)methanone 
• 1172074-20-2 1-benzyl-2-((4-(phenylsulfonyl)piperazin-1-yl)methyl)-1H-benzo[d]imidazole 
• 189560-86-9 1-benzyl-2-(piperazin-1-ylmethyl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.

Discovery of benzimidazole derivatives as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors with glucose consumption improving activity

Aldehyde dehydrogenase 1A1 (ALDH1A1) plays vital physiological and toxicological functions in many areas, such as CNS, inflammation, metabolic disorders, and cancers. Overexpression of ALDH1A1 has been disclosed to play an important role in obesity, diabetes and other diseases, indicating the potential need for the identification and development of small molecule ALDH1A1 inhibitors. Herein, a series of benzimidazole derivatives was designed, synthesized and evaluated. Among them, compounds 21, 27, 29, 61 and 65 exhibited excellent inhibitory activity against ALDH1A1 with IC50 values in the low micromolar range and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Moreover, an in vitro study demonstrated that all five compounds effectively improved glucose consumption in HepG2 cells, of which, 61 and 65 at 10 μM produced nearly equal glucose consumption with positive control Metformin (Met) at 1 mM. Furthermore, 61 and 65 showed desirable metabolic stability in human liver microsomes. All these results suggest that 61 and 65 are suitable for further studies.

Design, synthesis and biological evaluation of benzimidazole-rhodanine conjugates as potent topoisomerase II inhibitors

In this study, a series of benzimidazole-rhodanine conjugates were designed, synthesized and investigated for their topoisomerase II (Topo II) inhibitory and cytotoxic activities. The results from Topo II-mediated pBR322 DNA relaxation and cleavage assays showed that the synthesized compounds might act as Topo II catalytic inhibitors. Certain compounds displayed potent Topo II inhibition at 10 μM. The cytotoxic activities of these compounds against HeLa, A549, Raji, PC-3, MDA-MB-201, and HL-60 cancer cell lines were evaluated. The results indicated that these compounds exhibited strong antiproliferative activity. A good relationship was observed between the Topo II inhibitory potency and the cytotoxicity of these compounds. The structure-activity relationship revealed that the electronic effects, the phenyl group, and the rhodanine moiety were particularly important for the Topo II inhibitory potency and cytotoxicity.

Design, synthesis, and biological evaluation of novel thiazolidinediones as PPAR3/FFAR1 dual agonists

Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR3 is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR3 and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues.

"All-water" chemistry of tandem N-alkylation-reduction- condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

A water-assisted tandem N-alkylation-reduction-condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated 'electrophile-nucleophile dual activation' in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C-N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C-N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation-reduction-condensation process exemplifies an 'all-water' chemistry for the synthesis of N-arylmethyl-2- substituted benzimidazoles.

Alternate method for the synthesis of N-alkyl/aralkyl-2-(α-hydroxy alkyl/aralkyl)benzimidazoles via regiospecific acetylation

Acetylation of 1H-2-(α-hydroxyalkyl/aryl)benzimidazoles 2 with Ac2O results in the regiospecific formation of O-acetoxy derivative 3, which on alkylation with alkylating agents in nonaqueous media under phase-transfer catalytic conditions affords N-alkyl