7187-31-7

Usage

Uses

Used in Pharmaceutical Industry:
[1-(4-CHLOROBENZYL)-1H-BENZIMIDAZOL-2-YL]METHANOL is used as an antifungal agent for its potential to combat fungal infections. The presence of the chlorobenzyl group and the benzimidazole core in its structure contributes to its antifungal properties, making it a valuable compound in the development of new antifungal medications.
Used in Drug Research and Development:
In the realm of drug research and development, [1-(4-CHLOROBENZYL)-1H-BENZIMIDAZOL-2-YL]METHANOL serves as a key compound for exploring its potential applications in the pharmaceutical industry. Its unique structure and antifungal properties make it an attractive candidate for further investigation and experimentation, with the aim of discovering new therapeutic agents and treatments.
Used in Drug Delivery Systems:
As a methanol derivative, [1-(4-CHLOROBENZYL)-1H-BENZIMIDAZOL-2-YL]METHANOL may be utilized in drug delivery systems due to its solubility in polar solvents. This characteristic could facilitate the development of novel formulations for the delivery of pharmaceutical agents, potentially enhancing the efficacy and bioavailability of medications.
Used in Metabolism Studies:
The potential for [1-(4-CHLOROBENZYL)-1H-BENZIMIDAZOL-2-YL]METHANOL to be metabolized by the body suggests that it may have medicinal effects. As a result, it can be used in metabolism studies to better understand its interactions with the human body and to determine its potential as a therapeutic agent.

Upstream product

• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 33809-91-5 (1H-benzo[d]imidazol-2-yl)methyl acetate 
• 622-95-7 4-chlorobenzyl bromide 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 7189-18-6 1-(4-chlorobenzyl)-2-(chloromethyl)-1H-benzo[d]imidazole 
• 537010-34-7 1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbaldehyde 

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.

Evaluation of Cytotoxic Activity of New Benzimidazole-Piperazine Hybrids Against Human MCF-7 and A549 Cancer Cells

A series of benzimidazole-piperazine hybrids (14 – 37) were designed, synthesized and evaluated for their cytotoxic activity against human lung (A549) and breast (MCF-7) cancer cell lines. Preliminary evaluation revealed that most of these hybrid molecules (i.e., 16 – 25) exhibited noteworthy and preferential antiproliferative effect against human lung cancer (A549) with IC50 values of 2.8 – 7.8 μM. Among the synthesized molecules, compound 17 showed the most balanced cytotoxic effect against lung (A549) and breast (MCF-7) cancer cells with IC50 values of 5.4 and 4.2 μM, respectively. To explore the mechanistic aspects fundamental to the observed activity, further biological studies of compounds 16, 17 and 22 were carried out. In addition, these compounds induced PARP-1 cleavage and caspase 7 activation, caused morphological changes such as bleb formation in the treated cells, and significantly increased the nuclear fragmentation. Taken all together, our findings indicate that cytotoxic activities of newly synthesized benzimidazole-piperazine hybrids are mediated through the apoptotic cell death induction. These benzimidazole derivatives have the potential for further development as anticancer agents.

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.