537010-30-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is used as a building block for the synthesis of biologically active compounds due to its benzimidazole structure, which is a common structural motif in many pharmaceuticals. Its potential applications include the development of new drugs targeting various diseases and conditions.
Used in Organic Synthesis:
1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE serves as a key intermediate in the creation of various organic substances. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Reactions as a Reagent:
As a reagent, 1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is utilized in a range of chemical reactions to facilitate the formation of desired products. Its carbonyl group, in particular, can participate in various reactions, such as condensation, reduction, and oxidation processes.
Used in Material Science:
1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE may have applications in the development of new materials due to its unique chemical structure. It could potentially be incorporated into the design of advanced materials with specific properties, such as improved stability, reactivity, or selectivity.
Used in Specialty Chemicals Manufacturing:
1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE may also find use as a component in the manufacturing of specialty chemicals, where its unique structure and reactivity can be leveraged to produce high-value products with specific applications in various industries.

InChI:InChI=1/C16H14N2O/c1-12-6-8-13(9-7-12)10-18-15-5-3-2-4-14(15)17-16(18)11-19/h2-9,11H,10H2,1H3

Upstream product

• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 104-81-4 4-Methylbenzyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 46804-13-1 1‐(4‐methylbenzyl)benzimidazole 
• 104-82-5 4-Methylbenzyl chloride 
• 51-17-2 benzoimidazole 

Downstream Products

• 1394047-70-1 (E)-4-(2-(2-((1-(4-methylbenzyl)-1H-benzo[d]imidazol-2-yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine 

Relevant academic research and scientific papers

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 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.

Benzimidazole chalcone derivative, and preparation method and application thereof

The invention belongs to the technical field of drug synthesis, and especially relates to a benzimidazole chalcone derivative, and a preparation method and an application thereof. The structural formula of the benzimidazole chalcone derivative is represented by formula (I); and in the formula (I), R1 is fluorine or a methyl group, and R2 is selected from a nitro group, a cyano group, fluorine, chlorine, bromine, a methyl group, a methoxy group, a dimethoxy group, a trimethoxy group, an ethyl group and an isopropyl group. Results of studies show that the benzimidazole chalcone derivative of thepresent invention can target DNA topoisomerase II, can effectively inhibit the activity of human DNA topoisomerase II (TopoII), and can be used for preparing antitumor drugs with topoisomerase II asa target. The benzimidazole chalcone derivative of the present invention has a strong inhibitory effect on the proliferation of a plurality of tumor cells, and can be used for preparing anticancer drugs.

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 anticancer activity of 4-morpholinothieno[3,2-d]- pyrimidine derivatives bearing arylmethylene hydrazine moiety

Three series of 4-morpholinothieno[3,2-d]pyrimidine derivatives containing arylmethylene hydrazine moiety (11a-f, 13a-k and 15a-h) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (H460, HT-29, MDA-MB-231). Most of them exhibited moderate to significant cytotoxicity and high-selectivity against one or more cell lines, especially compounds 11c, 13b, 15f and 15g possessing dramatically increased cytotoxicity as compared with the positive controls, which were further evaluated for six other cancer cell lines and one normal cell line. The most promising compound 11c, bearing 3,4-methylenedioxy phenyl group, showed remarkable cytotoxicity against H460, HT-29 and MDA-MB-231 cell lines with IC50 values of 0.003 μM, 0.42 μM and 0.74 μM, which was 1.6- to 290-fold more potent than GDC-0941.