4856-97-7

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole-2-methanol is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form derivatives and participate in chemical reactions makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
1H-Benzimidazole-2-methanol is used as a starting material for the preparation of various chemical compounds, such as 2-(chloromethyl)-1-(methylsulfonyl)benzimidazole and 1H-benzimidazol-2-ylmethyl diethyl phosphate. These synthesized compounds have potential applications in different fields, including pharmaceuticals and materials science.

InChI:InChI=1/C8H8N2O/c11-5-8-9-6-3-1-2-4-7(6)10-8/h1-4,11H,5H2,(H,9,10)

Upstream product

• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 79-14-1 glycolic Acid 
• 95-54-5 1,2-diamino-benzene 
• 1865-09-4 ethyl 1H-benzimidazole-2-carboxylate 
• 108-45-2 m-phenylenediamine 
• 74586-46-2 [1-(1-Ethoxy-ethyl)-1H-benzoimidazol-2-yl]-methanol 
• 623-50-7 ethyl 2-hydroxyacetate 
• 615-28-1 o-phenylenediamine dihydrochloride 
• 56-40-6 glycine 
• 136526-34-6 (2-α-hydroxymethyl benzimidazolinium){MoOCl4*H2O} 
• 107-21-1 ethylene glycol 
• 25289-18-3 sodium glycolate 
• 56-81-5 glycerol 
• 51-17-2 benzoimidazole 

Downstream Products

• 156576-14-6 <1,4>oxazino 3-oxo<4,3-a>benzimidazole 
• 156576-12-4 3-methyl-1H-benzo[4,5]imidazo[2,1-c][1,4]oxazine 
• 118469-11-7 1-propargyl 2-hydroxymethylbenzimidazole 
• 156576-15-7 (1-amino-1H-benzimidazol-2-yl)methanol 
• 30770-24-2 2-(bromomethyl)-1,3-benzimidazole 
• 212503-29-2 1-(2,6-difluorobenzyl)-2-(2,6-difluorobenzyloxymethyl)benzimidazole 
• 14483-78-4 1H-benzimidazol-2-ylmethyl 4-chlorophenyl sulfide 
• 300706-95-0 (1-allyl-1H-benzo[d]imidazol-2-yl)methanol 
• 118482-08-9 1-vinylbenzimidazole-2-carboxaldehyde 
• 63633-05-6 1-vinyl-2-hydroxymethylbenzimidazole 

Relevant academic research and scientific papers

The construction of coordination networks based on imidazole-based dicarboxylate ligand containing hydroxymethyl group

Reaction of Cd(ii), Fe(ii), and Cu(ii) with a new ligand 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid (H4hmIDC) and 4,4′-bipyridine (bpy) affords three coordination polymers of {[Cd(H 2hmIDC)(bpy)]·0.5bpy·H2O}n (1), [Fe2(HhmIDC)2]n (2), and {[Cu 2(ITC)(bpy)(H2O)3]·2.5H 2O}n (3) (ITC = imidazole-2,4,5-tricarboxylic acid), respectively. Complex 1 and complex 3 are (4,4) nets in topological view and display in different packing mode, while hydroxymethyl group in complex 3 is oxidized to carboxylic group in situ. Complex 2 is a rare example of a cdl-e network containing both tetrahedral and square nodes. The hydroxymethyl groups act as a precursor and undergo different reactions directed by metal ions.

Synthesis, in-vitro cytotoxic activity and DNA interactions of new dicarboxylatoplatinum(II) complexes with 2-hydroxymethylbenzimidazole as carrier ligands

Objectives The aim of this study was to investigate the in-vitro cytotoxic activity of new platinum(II) complexes on the human HeLa (ER-), MCF-7 (ER+) and MDA-MB 231 (ER-) cell lines. Furthermore, we investigated plasmid DNA interactions and inhibition of BamHI and HindIII restriction enzyme activity of the complex 1-4,7. Methods Platinum(II) complexes were synthesised from precursor complexes of [PtL2Cl2] and [PtL2I2]. Their cytotoxic activity was tested by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Their plasmid DNA interactions and restriction enzyme activities were also investigated using the agarose gel electrophoresis method. Key findings The growth inhibitory effect results showed that the cytotoxicity of complex 2 was found to be the most active complex among the synthesised complexes. Conclusions The MTT results showed that complex 2 was found to be cytotoxic equal to cisplatin and higher than carboplatin against the MCF-7 and MDA-MB-231 cell lines. Furthermore, the estrogen or progesterone co-treatment slightly increased the cytotoxicity of complex 2, the cisplatin and carboplatin compared with the complex 2 tested alone in 50μm concentration. According to plasmid DNA interaction and the restriction studies, complexes 1-4,7 modified the tertiary structure of pBR322 plasmid DNA, and complexes 2-4 prevented enzyme digestion at high concentrations.

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.

A novel Trans-Pt(II) complex bearing 2-acetoxymethylbenzimidazole as a non-leaving ligand (trans-[Pt(AMBi)2Cl2]): Synthesis, antiproliferative activity, DNA interaction and molecular docking studies compared with its cis isomer (cis-[Pt(AMBi)2Cl2])

Trans-[Pt(AMBi)2Cl2 (1) in which AMBi is 2-acetoxymethylbenzimidazole, was synthesized and characterized by spectroscopic methods. Novel complex 1 was evaluated for its potential antiproliferative effect against three human cancer cell lines, including HeLa (human cervix cancer), MCF-7 (human breast cancer) and A549 (human non-small-cell lung cancer) in comparison with those of cis-[Pt(AMBi)2Cl2 (2) and cisplatin by means of the MTT assay. Interaction of complexes 1, 2 and cisplatin with pBR322 plasmid DNA and their restriction endonuclease reactions by BamHI and HindIII enzymes were studied by agarose gel electrophoresis. Cytotoxicity tests showed that complex 1 exhibited similar in vitro cytotoxicity profile as compared with cisplatin whereas better than corresponding cis isomer against MCF-7 and A549 human cancer cell lines. The electrophoretic mobility shift assay showed that although no comigration of the Form I and II bands of plasmid DNA was observed for complex 1 at the concentrations tested, the binding of complex 1 was able to prevent partially BamHI digestion for concentrations ranging from 40 to 160 μM while having no inhibitory effect on HindIII activity in the digestion studies with restriction enzymes. Molecular docking studies on DNA were carried out to explore the binding mode and the best orientation of the complexes 1 and 2 to DNA.

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

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.

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2

Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.

Polyheterocyclic substituted pyrimidines or pyridylamine derivatives Composition and medical application thereof

The invention discloses a polycyclic substituted pyrimidine or pyridine amine derivative, and the structure is shown in a formula (I). The invention further discloses a pharmaceutically acceptable salt of the derivative, a solvate, a stereoisomer, a prodrug, a pharmaceutical composition and and an application thereof in medicine. The compounds of the present invention have significant adenosine A. 2A Receptor and/or adenosine A2B The receptor antagonism activity is very practical.

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.

Design, synthesis and anti-tumor activity of novel benzimidazole-chalcone hybrids as non-intercalative topoisomerase II catalytic inhibitors

Chemical diversification of type II topoisomerase (Topo II) inhibitors remains indispensable to extend their anti-tumor therapeutic values which are limited by their side effects. Herein, we designed and synthesized a novel series of benzimidazole-chalcone hybrids (BCHs). These BCHs showed good inhibitory effect in the Topo II mediated DNA relaxation assay and anti-proliferative effect in 4 tumor cell lines. 4d and 4n were the most potent, with IC50values less than 5 μM, superior to etoposide. Mechanistic studies indicated that the BCHs functioned as non-intercalative Topo II catalytic inhibitors. Moreover, 4d and 4n demonstrated versatile properties against tumors, including inhibition on the colony formation and cell migration, and promotion of apoptosis of A549 cells. The structure-activity relationship and molecular docking analysis suggested possible contribution of the chalcone motif to the Topo II inhibitory and anti-proliferative potency. These results indicated that 4d and 4n could be promising lead compounds for further anti-tumor drug research.