537010-38-1

Basic information

• Product Name: 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE
• Synonyms: 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE;OTAVA-BB 1056453;1-(2-chlorobenzyl)-1H-benzimidazole-2-carbaldehyde(SALTDATA: FREE)
• CAS NO: 537010-38-1
• Molecular Formula: C₁₅H₁₁ClN₂O
• Molecular Weight: 270.71
• Mol File: 537010-38-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 476.9°C at 760 mmHg
• Flash Point: 242.2°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 2.93E-09mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE(537010-38-1)
• EPA Substance Registry System: 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE(537010-38-1)

Safety Data

• Hazardous Substances Data: 537010-38-1(Hazardous Substances Data)

Usage

Description

1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is a chemical compound characterized by the presence of a benzimidazole ring with a 2-chlorobenzyl group and a carbaldehyde functional group. 1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE has been studied for its potential as an antifungal and antibacterial agent, as well as for its use in the synthesis of various pharmaceutical compounds. The chlorobenzyl group may contribute to its ability to interact with biological targets and exhibit pharmacological activity, making it a versatile building block for the synthesis of diverse bioactive molecules with potential applications in drug discovery and development.

Uses

Used in Pharmaceutical Industry:
1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its unique structure and potential pharmacological activity.
Used in Antifungal Applications:
1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is used as an antifungal agent, potentially effective against a range of fungal infections. Its chemical structure allows it to interact with biological targets, making it a promising candidate for the development of new antifungal drugs.
Used in Antibacterial Applications:
1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE is also used as an antibacterial agent, showing potential in combating bacterial infections. The presence of the chlorobenzyl group may enhance its ability to target and disrupt bacterial cells, contributing to its antibacterial properties.
Used in Drug Discovery and Development:
1-(2-CHLOROBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE serves as a versatile building block in drug discovery and development, owing to its potential to be modified and incorporated into a variety of bioactive molecules with different therapeutic applications.

InChI:InChI=1/C15H11ClN2O/c16-12-6-2-1-5-11(12)9-18-14-8-4-3-7-13(14)17-15(18)10-19/h1-8,10H,9H2

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 51-17-2 benzoimidazole 

Downstream Products

• 1394047-72-3 (E)-4-(2-(2-((1-(2-chlorobenzyl)-1H-benzo[d]imidazol-2-yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine 
• 1394047-23-4 C₂₅H₂₂ClN₇OS 

Relevant articles and documents

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 3D-QSAR analysis of novel 2-hydrazinyl-4- morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4- morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q2 = 0.436, r2 = 0.937) and CoMSIA (q2 = 0.706, r2 = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents.