54255-79-7

Basic information

• Product Name: 1H-BENZIMIDAZOLE, 2-(2-CHLORO-5-NITROPHENYL)-
• Synonyms: 1H-BENZIMIDAZOLE, 2-(2-CHLORO-5-NITROPHENYL)-;2-(2-Chloro-5-nitrophenyl)-1H-benzo[d]imidazole
• CAS NO: 54255-79-7
• Molecular Formula: C₁₃H₈ClN₃O₂
• Molecular Weight: 273.67452
• Mol File: 54255-79-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 198-199 °C
• Boiling Point: 499°C at 760 mmHg
• Flash Point: 255.6°C
• Appearance: /
• Density: 1.485 g/cm³
• Vapor Pressure: 4.31E-10mmHg at 25°C
• Refractive Index: 1.718
• PKA: 10.68±0.10(Predicted)
• CAS DataBase Reference: 1H-BENZIMIDAZOLE, 2-(2-CHLORO-5-NITROPHENYL)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-BENZIMIDAZOLE, 2-(2-CHLORO-5-NITROPHENYL)-(54255-79-7)
• EPA Substance Registry System: 1H-BENZIMIDAZOLE, 2-(2-CHLORO-5-NITROPHENYL)-(54255-79-7)

Safety Data

• Hazardous Substances Data: 54255-79-7(Hazardous Substances Data)

Usage

Structure

Benzimidazole derivative with a chlorine atom and a nitro group attached to the phenyl ring

Usage

Pharmaceutical and agrochemical applications, building block in the synthesis of biologically active compounds

Potential as an anti-cancer agent

Yes, shows promise as a treatment for various types of cancer

Other properties

Antimicrobial and anti-inflammatory properties

Importance

Versatile and important chemical in the field of medicinal chemistry

InChI:InChI=1/C13H8ClN3O2/c14-10-6-5-8(17(18)19)7-9(10)13-15-11-3-1-2-4-12(11)16-13/h1-7H,(H,15,16)

Upstream product

• 54255-74-2 N-(2-aminophenyl)-2-chloro-5-nitrobenzamide 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 25784-91-2 2-chloro-5-nitrobenzoylchloride 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 313402-16-3 3-(1H-benzo[d]imidazol-2-yl)-4-chloroaniline 

Relevant articles and documents

Preparation method and application of antibacterial drugs

The invention provides phosphite ester compounds with an antibacterial effect and represented by a general formula I, a preparation method of the compounds, an application of the compounds in antibacterial drugs and pharmaceutical compositions containing the compounds. The ten synthesized compounds are novel in structure, the antibacterial activity of the compounds is equivalent to or even superior to that of positive control clindamycin and ciprofloxacin, the antibacterial spectrum is wide, and the compounds 5 and 10 are particularly expected to be further developed into antibacterial activedrugs.

N - 3 - benzimidazole thiazole derivative and its preparation method and application

The invention discloses a new compound N-3-benzimidazole thiazole amine derivative and a preparation method and application thereof. A structural formula of the compound is shown as in figure I, and in the figure I, R1 is morpholinyl, piperidyl, N-methyl piperazinyl, N-arylpiperazine, diethylin, ethyoxyl, (dimethoxy)ethylamino, or R1 is one of mono-substituted or multi-substituted aniline on the following benzene ring: fluorine, chlorine, trifluoromethoxyl, methyl, methoxyl, hydroxyl group, nitryl, amino group, acetamido, trifluoromethyl and cyano group. The compound disclosed by the invention has better antineoplastic activity, and can be used as a therapeutic agent for treating a tumor in the field of antineoplastic drug preparation.

Design, Synthesis, and Pharmacological Evaluation of 2-(2,5-Dimethyl-5,6,7,8-tetrahydroquinolin-8-yl)-N-aryl Propanamides as Novel Smoothened (Smo) Antagonists

A series of novel Smo antagonists were developed either by directly incorporating the basic skeleton of the natural product artemisinin or by first breaking artemisinin into structurally simpler and stable intermediates and then reconstructing into diversified heterocyclic derivatives, equipped with a Smo-targeting bullet. 2-(2,5-Dimethyl-5,6,7,8-tetrahydroquinolin-8-yl)-N-arylpropanamide 65 was identified as the most potent, with an IC50 value of 9.53 nM against the Hh signaling pathway. Complementary mechanism studies confirmed that 65 inhibits Hh signaling pathway by targeting Smo and shares the same binding site as that of the tool drug cyclopamine. Meanwhile, 65 has a good plasma exposure and an acceptable oral bioavailability. Dose-dependent antiproliferative effects were observed in ptch+/-;p53-/- medulloblastoma cells, and significant tumor growth inhibitions were achieved for 65 in the ptch+/-;p53-/- medulloblastoma allograft model.