193542-65-3

Basic information

• Product Name: 4-(4-CHLOROPHENYL)-4-HYDROXY-A,A-DIPHENYL-1-PIPERIDINEPENTANENITRILE HYDROCHLORIDE
• Synonyms: 4-(4-CHLOROPHENYL)-4-HYDROXY-A,A-DIPHENYL-1-PIPERIDINEPENTANENITRILE HYDROCHLORIDE;BX 513 HYDROCHLORIDE;4-(4-Chlorophenyl)-4-hydroxy-α,α-diphenyl-1-piperidinepentanenitrilehydrochloride;BX 513 HCL
• CAS NO: 193542-65-3
• Molecular Formula: C₂₈H₂₉ClN₂O
• Molecular Weight: 445
• Mol File: 193542-65-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Desiccate at +4°C
• CAS DataBase Reference: 4-(4-CHLOROPHENYL)-4-HYDROXY-A,A-DIPHENYL-1-PIPERIDINEPENTANENITRILE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-CHLOROPHENYL)-4-HYDROXY-A,A-DIPHENYL-1-PIPERIDINEPENTANENITRILE HYDROCHLORIDE(193542-65-3)
• EPA Substance Registry System: 4-(4-CHLOROPHENYL)-4-HYDROXY-A,A-DIPHENYL-1-PIPERIDINEPENTANENITRILE HYDROCHLORIDE(193542-65-3)

Safety Data

• Hazardous Substances Data: 193542-65-3(Hazardous Substances Data)

Usage

Biological Activity

Selective CCR1 receptor antagonist (K i values are 0.04, > 10, > 10 and > 10 nM for CCR1, CCR5, CXCR2 and CXCR4 receptors respectively). Inhibits MIP-1 α -induced intracellular calcium mobilization (IC 50 = 2.5 μ M). Also a full inverse agonist at US28, a? HCMV-encoded chemokine receptor.

Upstream product

• 39512-49-7 4-(4-chlorophenyl)-4-hydroxypiperidine 
• 14078-27-4 α-(3-bromopropyl)-α-phenyl-benzeneacetonitrile 
• 1705-68-6 5-hydroxy-2,2-diphenylpentanenitrile 
• 86-29-3 Diphenylacetonitrile 
• 1585-11-1 5-chloro-2,2-diphenylpentanenitrile 

Downstream Products

• 193541-41-2 phenyl N-[5-[4-(4-chlorophenyl)-4-hydroxypiperidino]-2,2-diphenylpentyl]carbamate 
• 182807-84-7 VUF 5728 

Relevant articles and documents

Catalytic Formal Conjugate Addition: Direct Synthesis of δ-Hydroxynitriles from Nitriles and Allylic Alcohols

Alcohols and nitrile functionalities have widespread applications in biochemical and chemical synthesis. Catalytic transformations involving C-C bond formation relying on unsaturated coupling partners create important pathways for processes in synthetic, material, and medicinal chemistry. The discovery of a simple and selective coupling of nitriles with allylic alcohols catalyzed by a ruthenium pincer complex is described, which tolerates reactive functional groups such as carbamate, sulfonate, olefin, cyano, and trifluoromethyl-substituted benzyl nitriles. Homo allylic alcohols also provided 1,4-addition products following the isomerization of double bonds. Mechanistic studies supported that the allylic alcohols initially undergo selective oxidation by the catalyst to α,β-unsaturated carbonyl compounds followed by 1,4-conjugate addition of benzyl nitriles catalyzed by a base and subsequent catalytic reduction of carbonyl functionality, leading to the formation of δ-hydroxynitrile products. The catalytic cycle of this tandem process is established by density functional theory studies. Remarkably, anipamil drug is successfully synthesized using this catalytic protocol. The utility of the δ-hydroxynitrile products in the synthesis of biologically active molecules and their further functionalization are also demonstrated.

Methods of Inhibiting Metastasis from Cancer

The present invention includes compositions that are useful in preventing or treating metastasis in a subject diagnosed with cancer. The present invention also includes methods of preventing or treating metastasis in a subject diagnosed with cancer, where

Discovery of novel non-peptide CCR1 receptor antagonists

Ligands for the CCR1 receptor (MIP-1α and RANTES) have been implicated in a number of chronic inflammatory diseases, most notably multiple sclerosis and rheumatoid arthritis. Because these ligands share a common receptor, CCR1, we sought to discover antagonists for this receptor as an approach to treating these disorders. A novel series of 4-hydroxypiperidines has been discovered by high throughput screening (HTS) which potently inhibits the binding of MIP-1α and RANTES to the recombinant human CCR1 chemokine receptor. The structure-activity relationships of various segments of this template are described as the initial HTS lead 1 was optimized synthetically to the highly potent receptor antagonist 6s. This compound has been shown to have at least 200-fold selectivity for inhibition of CCR1 over other human 7- TM receptors, including other chemokine receptors. In addition, data obtained from in vitro functional assays demonstrate the functional antagonism of compound 6s and structurally related analogues against the CCR1 receptor in a concentration dependent manner. The discovery and optimization of potent and selective CCR1 receptor antagonists represented by compound 6s potentially represent a novel approach to the treatment of chronic inflammatory diseases.