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

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 
• 25784-91-2 2-chloro-5-nitrobenzoylchloride 
• 95-54-5 1,2-diamino-benzene 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 

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.

Comprising benzimidazole structure of sulfonamide derivatives and its preparation and use

The invention belongs to the field of medical technology, discloses benzimidazole structure of sulfonamide derivatives and its preparation method and application. The derivatives of formula I as shown in the structural formula, in formula I, R1 , R2 , R3 , R4 , X such as the claim and the specification. The compounds of the invention has better anti-tumor activity, can be used as a therapeutic agent for the treatment of tumor, it is also SMO inhibitors. (Type I).

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.

Nicotinamide derivative and preparation method and application thereof

The invention discloses a novel compound N-3-(4-R2 substituted)-(1-R-substituted benzimidazole)-(1'-R3 substituted)-2'-oxa-nicotinamide derivative, and a preparation method and an application thereof.The structural formula of the compound is as shown in a formula I, in which R1, R2 and R3 are described in the claims and description. The compound has very good anti-diabetes activity, and can be used as therapeutic agent for treating diabetes in the field of preparing anti-diabetes drugs. The formula is as shown in the description.

A second group of the benzimidazole aryl amide compound and its synthesis and use

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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.

Synthesis and evaluation of novel N-3-benzimidazolephenylbisamide derivatives for antiproliferative and Hedgehog pathway inhibitory activity

A series of novel N-3-benzimidazolephenylbisamide derivatives bearing the 4-benzyloxyphenyl moiety were synthesized and evaluated for their antiproliferative activity against MGC803, HT29, MKN45 and SW620 cancer cell lines in vitro. The pharmacological data demonstrated that the majority of the target compounds exhibited higher efficacy against MGC803, HT29 and MKN45 cells, among which compound 7m displayed higher antiproliferative activity than vismodegib. Furthermore, compound 7m manifested better inhibition of the Hedgehog (Hh) signaling pathway in different Hh-related assays and may compete with boron-dipyrromethene (BODIPY)-cyclopamine for binding to the human smoothened (Smo) receptor. In addition, molecular docking studies suggested that compound 7m interacts very closely with the vismodegib docking pose through hydrogen bonds at the taladegib binding site of the Smo receptor.

Synthesis and biological evaluation of SANT-2 and analogues as inhibitors of the hedgehog signaling pathway

Hedgehog (Hh) signaling plays an important role in cell signaling of embryonic development and adult tissue homeostasis. In vertebrates, the hh gene encodes three different unique proteins: sonic hedgehog (Shh), desert hedgehog (Dhh) and indian hedgehog (Ihh). Disruption of the Hh signaling pathway leads to severe disorders in the development of vertebrates whereas aberrant activation of the Hh pathway has been associated with several malignancies including Gorlin syndrome (a disorder predisposing to basal cell carcinoma, medulloblastoma and rhabdomyosarcoma), prostate, pancreatic and breast cancers. In vivo evidence suggests the antagonism of excessive Hh signaling provides a route to unique mechanism-based anti-cancer therapies. Recently the small molecule SANT-2 was identified as a potent antagonist of Hh-signaling pathway. Here, we describe the synthesis, SAR studies as well as biological evaluation of SANT-2 and its analogues. Fifteen SANT-2 derivatives were synthesized and analyzed for their interference with the expression of the Hh target gene Gli1 in a reporter gene assay. By comparison of structure and activity important molecular descriptors for Gli inhibition could be identified. Furthermore we identified derivative TC-132 that was slightly more potent than the parent compound SANT-2. Selected compounds were tested for Hh related teratogenic effects in the small teleost model medaka. Albeit Gli expression has indicated a 16-fold higher Hh-inhibiting activity than observed for the plant alkaloid cyclopamine, none of the tested compounds were able to induce the cyclopamine-specific phenotype in the medaka assay.