7191-71-1

Usage

Uses

Used in Pharmaceutical Research:
2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole is used as a research compound for exploring its potential biological activities. 2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole's unique structure, featuring a chloromethyl and a fluorobenzyl group, may contribute to its reactivity or binding affinity with biological targets, which is crucial for the development of new drugs.
Used in Medicinal Chemistry:
2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole is used as a starting material or intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its benzo[d]imidazole core, along with the chloromethyl and fluorobenzyl groups, can be further modified to create derivatives with enhanced properties, such as improved potency, selectivity, or bioavailability.
Used in Antimicrobial Applications:
2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole is used as an antimicrobial agent, leveraging the known antimicrobial properties of benzo[d]imidazole derivatives. 2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole's structure may allow it to target specific microorganisms or disrupt essential cellular processes, making it a potential candidate for the development of new antimicrobial drugs.
Used in Anticancer Applications:
2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole is used as a potential anticancer agent, given the interest in benzo[d]imidazole derivatives for their anticancer properties. 2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole may exhibit cytotoxic effects on cancer cells or interfere with cancer-related signaling pathways, warranting further investigation into its potential as a therapeutic agent for cancer treatment.
Used in Anti-inflammatory Applications:
2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole is used as an anti-inflammatory agent, building on the anti-inflammatory properties observed in some benzo[d]imidazole derivatives. 2-(chloromethyl)-1-(4-fluorobenzyl)-1H-benzo[d]imidazole may help modulate the immune response or reduce inflammation, making it a candidate for the development of new anti-inflammatory drugs.

Upstream product

• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 459-46-1 4-Fluorobenzyl bromide 
• 7191-70-0 N-(4''-fluorobenzyl)-1,2-phenylenediamine 
• 79-11-8 chloroacetic acid 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 59530-15-3 1-(4-fluoro-benzyl)-2-(4-propyl-piperazin-1-ylmethyl)-1H-benzoimidazole 

Relevant academic research and scientific papers

Design, Synthesis and Antimicrobial Evaluation of Novel Benzimidazole-incorporated Naphthalimide Derivatives as Salmonella typhimurium DNA Intercalators, and Combination Researches

Objective: A series of novel benzimidazole-incorporated naphthalimide derivatives were designed and prepared in an effort to overcome the increasing antibiotic resistance. Methods: The target novel benzimidazole-incorporated naphthalimide derivatives were synthesized from commercial 4-bromo-1,8-naphthalic anhydride and o-phenylene diamine by aminolysis, N-alkylation and so on. The antimicrobial activity of the synthesized compounds was evaluated in vitro by a two-fold serial dilution technique. The interaction of compound 10g with Salmonella typhimuri-um DNA was studied using UV-vis spectroscopic methods. Results: Compound 10g bearing a 2,4-dichlorobenzyl moiety exhibited the best antimicrobial activities in this series relatively; especially, it exhibited comparable activity against Salmonella typhi-murium in comparison with the reference drug Norfloxacin (MIC = 4 μg/mL). Further research showed that compound 10g could effectively intercalate into the Salmonella typhimurium DNA to form the 10g–DNA complex, which might correlate with the inhibitory activity. Molecular docking results demonstrated that naphthalimide compound 10g could interact with base-pairs of DNA hex-amer duplex by π–π stacking. Additionally, the combination of the strong active compound with clinical drugs exhibited better antimicrobial efficiency with less dosage and broader antimicrobial spectrum than the separate use of them alone. Notably, these combined systems were more sensitive to Fluconazole-insensitive M. ruber. Conclusion: This work provides a promising starting point to optimize the structures of benzimidaz-ole-incorporated naphthalimide derivatives as potent antimicrobial agents.

Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove

A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus (MIC = 4 μg/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c–DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity.

Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug-Resistant Pseudomonas aeruginosa DNA

A series of benzimidazole–quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2-fluorobenzyl derivative 5 b (ethyl 7-chloro-6-fluoro-1-[[1-[(2-fluorophenyl)methyl]benzimidazol-2-yl]methyl]-4-oxo-quinoline-3-carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep-2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV–DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b. Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug-resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities.

Astemizole analogues with reduced hERG inhibition as potent antimalarial compounds

Astemizole is a H1-antagonist endowed with antimalarial activity, but has hERG liabilities. Systematic structural modifications of astemizole led to the discovery of analogues that display very potent activity as inhibitors of the growth of the Plasmodium parasite, but show a decreased hERG inhibition, when compared to astemizole. These compounds can be used as starting point for the development of a new class of antimalarials.

Synthesis and Cytotoxic Evaluation of Pyrrole Hetarylazoles Containing Benzimidazole/Pyrazolone/1,3,4-Oxadiazole Motifs

Azomethine-linked pyrrole bishetarylazoles containing benzimidazole/pyrazolone/1,3,4-oxadiazole were synthesized in satisfactory yields. Their structures were confirmed by IR,1H-NMR,13C-NMR, and elemental analysis. Evaluation for the cytotoxic activities in vitro against a panel of breast cancer cell lines (MDA-AB-231, BT-474, and Ishikawa cells) revealed that the pyrrole–benzimidazole hybrids are more potent than the pyrazolone and 1,3,4-oxadiazole hybrids in all cell lines. Compound 9 displayed promising cytotoxicity against BT-474 cell line with IC50values, 7.7 μM.

Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents

A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 μM concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities.