401567-00-8

Basic information

• Product Name: 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI)
• Synonyms: 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI);2-chloro-1H-1,3-benzodiazole-5-carbonitrile;1H-BenziMidazole-6-carbonitrile,2-chloro-;2-Chloro-1H-benzimidazole-5-carbonitrile;2-Chloro-1H-benzimidazole-6-carbonitrile;2-chlorobenziMidazole-5-carbonitrile;2-Chloro-1H-benzo[d]iMidazole-5-carbonitrile
• CAS NO: 401567-00-8
• Molecular Formula: C₈H₄ClN₃
• Molecular Weight: 177.594
• Product Categories: BENZIMIDAZOLE
• Mol File: 401567-00-8.mol

Chemical Properties

• Boiling Point: 423.518 °C at 760 mmHg
• Flash Point: 209.936 °C
• Appearance: /
• Density: 1.505 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI)(401567-00-8)
• EPA Substance Registry System: 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI)(401567-00-8)

Safety Data

• Hazardous Substances Data: 401567-00-8(Hazardous Substances Data)

Usage

Uses

1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI) is used as a research chemical for the development of pharmaceuticals and other synthetic substances. 1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI)'s reactivity, due to the presence of the carbonitrile group, and its structural features make it a valuable candidate for various applications in the chemical and pharmaceutical industries.
Used in Pharmaceutical Research:
1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI) is used as a building block or intermediate in the synthesis of potential drug candidates. Its unique molecular structure and reactivity contribute to the development of new therapeutic agents.
Used in Chemical Research:
1H-Benzimidazole-5-carbonitrile,2-chloro-(9CI) is used as a reagent or catalyst in various chemical reactions, allowing for the synthesis of a wide range of compounds with potential applications in different industries.

InChI:InChI=1/C8H4ClN3/c9-8-11-6-2-1-5(4-10)3-7(6)12-8/h1-3H,(H,11,12)

Upstream product

• 221289-88-9 2-hydroxybenzimidazole-5-carbonitrile 
• 17626-40-3 4-cyano-1,2-phenylenediamine 
• 221289-88-9 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile 

Downstream Products

• 401567-01-9 3-{(2S,4S)-1-benzyloxycarbonyl-4-[4-(5-cyanobenzimidazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine 
• 1219813-91-8 6-(7-cyano-2,3-dihydrobenzo[d]oxazolo[3,2-a]imidazol-2-yl)hexyl 4-methylbenzenesulfonate 
• 1219813-92-9 6-(6-cyano-2,3-dihydrobenzo[d]oxazolo[3,2-a]imidazol-2-yl)hexyl 4-methylbenzenesulfonate 

Relevant articles and documents

BENZIMIDAZOLE DERIVATIVES AND THEIR USES

The present invention relates to inhibitors of Transient Receptor Potential Channel 6 (TRPC6) protein activity. The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising

METALLOENZYME INHIBITOR COMPOUNDS

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Fused bicyclic heteroarylpiperazine-substituted l-prolylthiazolidines as highly potent DPP-4 inhibitors lacking the electrophilic nitrile group

Hypoglycemic agents with a mechanism of depeptidyl peptidase IV (DPP-4) inhibition are suitable for once daily oral dosing. It is difficult to strike a balance between inhibitory activity and duration of action in plasma for inhibitors bearing an electrophilic nitrile group. We explored fused bicyclic heteroarylpiperazine substituted at the γ-position of the proline structure in the investigation of l-prolylthiazolidines lacking the electrophilic nitrile. Among them, 2-trifluoroquinolyl compound 8g is the most potent, long-lasting DPP-4 inhibitor (IC50 = 0.37 nmol/L) with high selectivity against other related peptidases. X-ray crystal structure determination of 8g indicates that CH-π interactions generated between the quinolyl ring and the guanidinyl group of Arg358 enhances the DPP-4 inhibitory activity and selectivity.

2-Phenylamino-6-cyano-1H-benzimidazole-based isoform selective casein kinase 1 gamma (CK1γ) inhibitors

Screening of the Amgen compound library led to the identification of 2-phenylamino-6-cyano-1H-benzimidazole 1a as a potent CK1 gamma inhibitor with excellent kinase selectivity and unprecedented CK1 isoform selectivity. Further structure-based optimization of this series resulted in the discovery of 1h which possessed good enzymatic and cellular potency, excellent CK1 isoform and kinase selectivity, and acceptable pharmacokinetic properties.

Design, syntheses, and structure-activity relationships of novel NPY Y5 receptor antagonists: 2-{3-Oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole derivatives

Design, syntheses, and structure-activity relationships of a novel class of 2-{3-oxospiro[isobenzofuran-1(3H),4′-piperidin]-1′-yl}benzimidazole NPY Y5 receptor antagonists are described. The benzimidazole structures were newly designed based on the urea linkage of our prototype Y5 receptor antagonists (2 and 3). By optimizing substituents on the benzimidazole core part of the lead compound 5a, we were able to develop a potent, orally available, and brain-penetrable Y5 selective antagonist (5k). Crown Copyright

Design of potent, orally available antagonists of the transient receptor potential vanilloid 1. Structure-activity relationships of 2-piperazin-1-yl-1H- benzimidazoles

The vanilloid receptor-1 (VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2- ylpiperazin-1-yl)-1H-benzo-[d]imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant (CFA).

BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.