1063712-34-4

Basic information

• Product Name: 2-Chloro-4-formylphenylboronic acid
• Synonyms: 2-Chloro-4-formylphenylboronic acid
• CAS NO: 1063712-34-4
• Molecular Formula: C₇H₆BClO₃
• Molecular Weight: 184.38474
• Mol File: 1063712-34-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 375.1±52.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerated.
• PKA: 7.05±0.58(Predicted)
• CAS DataBase Reference: 2-Chloro-4-formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-formylphenylboronic acid(1063712-34-4)
• EPA Substance Registry System: 2-Chloro-4-formylphenylboronic acid(1063712-34-4)

Safety Data

• Hazardous Substances Data: 1063712-34-4(Hazardous Substances Data)

Usage

Uses

2-Chloro-4-formylphenylboronic Acid is used as a reactant in the preparation of antitumor adamantyl-substituted retinoid-derived molecules that interact with orphan nuclear receptors.

Upstream product

• 1063712-33-3 2-(4-bromo-3-chlorophenyl)-1,3-dioxolane 

Downstream Products

• 1063712-40-2 2-(1-adamantyl)-4-(2'-chloro-4'-formylphenyl)acetanilide 

Relevant articles and documents

Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: Effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of Src homology 2 domain-containing protein tyrosine phosphatase-2 activity

(E)-4-[3-(1-Adamantyl)-4′-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell-cycle arrest and apoptosis of leukemia and cancer cells. Studies demonstrated that 3-Cl-AHPC bound to the atypical orphan nuclear receptor small heterodimer partner (SHP). Although missing a DNA-binding domain, SHP heterodimerizes with the ligand-binding domains of other nuclear receptors to repress their abilities to induce or inhibit gene expression. 3-Cl-AHPC analogues having the 1-adamantyl and phenolic hydroxyl pharmacophoric elements replaced with isosteric groups were designed, synthesized, and evaluated for their inhibition of proliferation and induction of human cancer cell apoptosis. Structure-anticancer activity relationship studies indicated the importance of both groups to apoptotic activity. Docking of 3-Cl-AHPC and its analogues to an SHP computational model that was based on the crystal structure of ultraspiracle complexed with 1-stearoyl-2-palmitoylglycero-3-phosphoethanolamine suggested why these 3-Cl-AHPC groups could influence SHP activity. Inhibitory activity against Src homology 2 domain-containing protein tyrosine phosphatase 2 (Shp-2) was also assessed. The most active Shp-2 inhibitor was found to be the 3′-(3,3-dimethylbutynyl) analogue of 3-Cl-AHPC.