4887-94-9

Basic information

• Product Name: 1H-Benzimidazole,2-chloro-5-methyl-(9CI)
• Synonyms: 1H-Benzimidazole,2-chloro-5-methyl-(9CI);2-CHLORO-5-METHYLBENZIMIDAZOLE;2-chloro-5-methyl-1H-benzimidazole();2-chloro-6-methyl-1H-benzimidazole;2-chloro-5-methyl-1H-benzo[d]imidazole
• CAS NO: 4887-94-9
• Molecular Formula: C₈H₇ClN₂
• Molecular Weight: 166.61
• Product Categories: BENZIMIDAZOLE
• Mol File: 4887-94-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1H-Benzimidazole,2-chloro-5-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,2-chloro-5-methyl-(9CI)(4887-94-9)
• EPA Substance Registry System: 1H-Benzimidazole,2-chloro-5-methyl-(9CI)(4887-94-9)

Safety Data

• Hazardous Substances Data: 4887-94-9(Hazardous Substances Data)

Usage

Description

1H-Benzimidazole,2-chloro-5-methyl-(9CI) is an organic compound belonging to the benzimidazole family. It is characterized by a fused imidazole and benzene ring structure, with a chlorine atom at the 2nd position and a methyl group at the 5th position. 1H-Benzimidazole,2-chloro-5-methyl-(9CI) is known for its potential applications in the pharmaceutical and chemical industries due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,2-chloro-5-methyl-(9CI) is used as a key intermediate in the design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors. These inhibitors serve as anti-prostate cancer drugs, targeting the PCA-1 enzyme that plays a role in cancer cell survival and proliferation. 1H-Benzimidazole,2-chloro-5-methyl-(9CI)'s unique structure allows for the development of potent and selective inhibitors, offering a promising therapeutic approach for prostate cancer treatment.
Used in Chemical Synthesis:
1H-Benzimidazole,2-chloro-5-methyl-(9CI) is also utilized in the synthesis of unsymmetrical 2,2’-bisbenzimidazole sulfide, a compound of pharmacological interest. The synthesis of this compound involves the use of 1H-Benzimidazole,2-chloro-5-methyl-(9CI) as a starting material, which can be further modified and functionalized to create novel molecules with potential applications in the pharmaceutical industry. The versatility of this compound in chemical synthesis makes it a valuable building block for the development of new drugs and therapeutic agents.

Upstream product

• 5400-75-9 5-methyl-1,3-dihydro-2H-benzimidazol-2-one 
• 496-72-0 4-methyl-1,2-diaminobenzene 

Downstream Products

• 1453097-57-8 C₁₈H₁₆N₄O 
• 1453097-59-0 C₂₃H₁₈N₄O 
• 1453097-13-6 1-(5-methyl-1H-benzimidazol-2-yl)-3-methyl-4-(phenylmethyl)-1H-pyrazol-5-ol 
• 93102-21-7 2-hydrazinyl-5-methyl-1H-benzo[d]imidazole 
• 1453097-22-7 C₂₀H₁₇F₃N₄O 
• 1453097-38-5 C₂₀H₂₀N₄O₂ 
• 1453097-21-6 4-[(3,4-dichlorophenyl)methyl]-3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-5-ol 
• 1453097-37-4 C₁₉H₁₇ClN₄O 
• 1453097-19-2 4-[(4-chlorophenyl)methyl]-3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-5-ol 
• 1453097-36-3 C₁₉H₁₇FN₄O 
• 1453097-24-9 4-[[4-(1,1-dimethylethyl)phenyl]methyl]-3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-5-ol 
• 1453097-20-5 3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-4-[(4-phenylphenyl)methyl]-1H-pyrazol-5-ol 

Relevant articles and documents

NOVEL BENZIMIDAZOLE DERIVATIVE AND USE THEREFOR

To provide a compound that has excellent oral absorbency and can inhibit Prostate Cancer Antigen-1(PCA-1) enzyme activity.SOLUTION: The present invention provides a compound represented by formula (I) or a pharmaceutically acceptable salt thereof. (Ris H,

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.

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.