2033-29-6

Basic information

• Product Name: 5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one
• Synonyms: 5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one;5,6-Dichloro-1,3-Dihydro-2h-BenziMidazol-2-One;2-Benzimidazolinone, 5,6-dichloro-;5,6-dichloro-1,3-dihydrobenzimidazol-2-one
• CAS NO: 2033-29-6
• Molecular Formula: C₇H₄Cl₂N₂O
• Molecular Weight: 203.02546
• Mol File: 2033-29-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 345 °C
• Boiling Point: 194.9±33.0 °C(Predicted)
• Appearance: /
• Density: 1.549±0.06 g/cm3(Predicted)
• Storage Temp.: Room temperature.
• PKA: 9.94±0.30(Predicted)
• CAS DataBase Reference: 5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one(2033-29-6)
• EPA Substance Registry System: 5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one(2033-29-6)

Safety Data

• Hazardous Substances Data: 2033-29-6(Hazardous Substances Data)

Usage

General Description

5,6-Dichloro-1H-benzo[d]imidazol-2(3H)-one, also known as DCBIO, is a synthetic compound with the chemical formula C7H3Cl2N2O. It is a heterocyclic organic compound that contains a benzimidazole ring system, which is commonly found in pharmaceuticals and agrochemicals. DCBIO has been studied for its potential as an anticancer agent, specifically for its ability to inhibit the growth of cancer cells by targeting the cell cycle and inducing apoptosis. It has also shown promising results in preclinical studies for the treatment of drug-resistant cancers and has demonstrated activity against a variety of cancer types, including breast, prostate, and lung cancer. Therefore, this compound holds potential for further development as a novel anticancer therapeutic agent.

Upstream product

• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 57-13-6 urea 
• 530-62-1 1,1'-carbonyldiimidazole 
• 64269-79-0 Carbonyldiimidazole 

Downstream Products

• 142372-26-7 1-benzyl-2,5,6-trichlorobenzimidazole 
• 1268713-06-9 N-(cyclohexylmethyl)-1-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)piperidine-4-carboxamide 
• 1268709-74-5 N-cyclopentyl-1-(5,6-dichloro-1-phenyl-1H-benzo[d]imidazol-2-yl)piperidine-4-carboxamide 
• 1268709-65-4 N-cyclopentyl-1-(5,6-dichloro-1-(1-phenylethyl)-1H-benzo[d]imidazol-2-yl)piperidine-4-carboxamide 
• 1268712-25-9 (R)-1-(5,6-dichloro-1-p-tolyl-1H-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide 
• 1268710-95-7 (R)-1-(5,6-dichloro-1-(3-methoxyphenyl)-1H-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide 
• 1268710-29-7 1-(1-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5,6-dichloro-1H-benzo[d]imidazol-2-yl)-N-cyclopentylpiperidine-4-carboxamide 
• 161468-75-3 5,6-Dichloro-2,3-dihydro-2-oxo-3-(phenylmethyl)-1H-benzimidazole-1-carboxylic acid ethyl ester 
• 1026027-09-7 5,6-Dichloro-3-cyclohexylmethyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester 
• 16865-11-5 2,5,6-trichloro-1H-benzo[d]imidazole 

Relevant articles and documents

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2

Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.

MEGLUMINE SALT FORMULATIONS OF 1-(5,6-DICHLORO-1H-BENZO[D]IMIDAZOL-2-YL)-1H-PYRAZOLE-4-CARBOXYLIC ACID

The meglumine salt of 1-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)-1H-pyrazole-4-carboxylic acid (compound (1)) and pharmaceutically acceptable formulations thereof are described. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by prolyl hydroxylase activity.