524937-24-4

Upstream product

• 3943-94-0 (E)-ethyl 2-hydroxycinnamate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 188112-72-3 trifluoromethanesulfonic acid 2-chloro-4-formylphenyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 159526-67-7 (E)-3-(4-benzyloxy-3-chlorophenyl)acrylic acid ethyl ester 
• 66422-84-2 4-benzyloxy-3-chlorobenzaldehyde 
• 2420-16-8 4-hydroxy-3-chlorobenzaldehyde 
• 103909-79-1 ethyl (E)-3-chloro-4-hydroxycinnamate 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 524937-26-6 ethyl (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamate 
• 1063712-51-5 ethyl (E)-[3'-(1-adamantyl)-4'-fluorophenyl]-3-chlorocinnamate 
• 1063712-76-4 ethyl (E)-4-[4'-benzyloxy-3'-(2,6-dimethylphenyl)phenyl]-3-chlorocinnamate 
• 1063712-96-8 ethyl (E)-4-[4'-benzyloxy-3'-(1-methylcyclohexyl)phenyl]-3-chlorocinnamate 
• 1063713-04-1 ethyl (E)-4-[4'-benzyloxy-3'-(3,5-dimethyl-1-adamantyl)phenyl]-3-chlorocinnamate 
• 1063713-14-3 ethyl (E)-3-chloro-4-[4'-hydroxy-3'-(2-methyl-1,3-dithian-2-yl)phenyl]cinnamate 
• 1063713-27-8 ethyl (E)-4-[4'-benzyloxy-3'-(1,1-diethylpropyl)phenyl]-3-chlorocinnamate 
• 1160658-23-0 (E)-ethyl 3-[5'-(adamant-1-yl)-4'-(tert-butyldimethylsilyloxy)-2-chloro-2'-methylbiphenyl-4-yl]acrylate 
• 943141-71-7 N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide 
• 943141-70-6 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamic acid 
• 943141-64-8 5-{3-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]-(2E)-2-propenylidene}-2,4-thiazolidinedione 
• 943141-63-7 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamaldehyde 
• 943141-62-6 (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamyl alcohol 

Relevant academic research and scientific papers

Highly twisted adamantyl arotinoids: Synthesis, antiproliferative effects and RXR transactivation profiles

Retinoid-related molecules with an adamantyl group (adamantyl arotinoids) have been described with selective activities towards the retinoid receptors as agonists for NR1B2 and NR1B3 (RARβ,γ) (CD437, MX3350-1) or RAR antagonists (MX781) that induce growth arrest and apoptosis in cancer cells. Since these molecules induce apoptosis independently of RAR transactivation, we set up to synthesize novel analogs with impaired RAR binding. Here we describe adamantyl arotinoids with 2,2′-disubstituted biaryl rings prepared using the Suzuki coupling of the corresponding fragments. Those with cinnamic and naphthoic acid end groups showed significant antiproliferative activity in several cancer cell lines, and this effect correlated with the induction of apoptosis as measured by caspase activity. Strikingly, some of these compounds, whereas devoid of RAR binding capacity, were able to activate RXR.

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.

An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: Effects of modifying its carboxylate group on apoptosis, proliferation, and

Apoptotic and antiproliferative activities of small heterodimer partner (SHP) nuclear receptor ligand (E)-4-[3′-(1-adamantyl)-4′- hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC), which was derived from 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2-naphthalenec

Induction of apoptosis in cancer cells

The present invention provides compounds that are inducers or inhibitors of apoptosis or apoptosis preceded by cell-cycle arrest. In addition, the present invention provides pharmaceutical compositions and methods for treating mammals with leukemia or other forms of cancer or for treating disease conditions caused by apoptosis of cells.