864175-69-9

Upstream product

• 1623-95-6 4-phenoxybenzoyl chloride 
• 62-53-3 aniline 
• 425366-11-6 (4-phenoxy-phenylmethylidyne)-phenyl-ammonium 
• 425365-94-2 4-phenoxy-N-phenyl-benzimidic acid 4-cyano-phenyl ester 
• 591-50-4 iodobenzene 
• 619-57-8 p-hydroxybenzamide 
• 2215-77-2 4-Phenoxybenzoic acid 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 31994-68-0 4-phenoxybenzoic acid ethyl ester 

Downstream Products

• 425365-94-2 4-phenoxy-N-phenyl-benzimidic acid 4-cyano-phenyl ester 
• 425366-11-6 (4-phenoxy-phenylmethylidyne)-phenyl-ammonium 

Relevant academic research and scientific papers

Design, synthesis, and structure-activity relationship studies of novel diaryl ether amides as potential antitumor agents

Sorafenib is a drug that has been verified to be effective on hepatoma cells. Three series of diaryl ethers have been designed and synthesized based on the structure of sorafenib. The 5m compound shows better inhibitory potency against HepG2 cells (IC50 = 1.96 μM) than sorafenib (IC50 = 9.61μM). These results have been verified with MTT assay and colony-forming assay. Moreover, compound 5m exhibits good antitumor activities against PLC/PRF5, HeLa, A549, and HT-29 cell lines. The excellent bioactivity of compound 5m confirms that a single optical conformation is superior to the racemate. A western blotting analysis indicates that compound 5m induces the apoptosis of HepG2 cells by enhancing the protein levels of p21 and Cl-caspase3.

Structure-based design, structure-activity relationship analysis, and antitumor activity of diaryl ether derivatives

To identify novel therapeutic agents to treat cancer, we synthesized a series of diaryl ether derivatives. Structure-activity relationship studies revealed that the presence of a chlorine or hydroxyl at the para-position on the phenyl ring (5h or 5k) significantly enhanced antitumor activity. Compound 5h had stronger growth inhibitory activity in HepG2, A549, and HT-29 cells than compound 5k, with IC50 values of 2.57, 5.48, and 30.04 μM, respectively. Compound 5h also inhibited the growth of other cells lines, including Hep3B, PLC/PRF5, SMMC-7721, HeLa, and A375, with IC50 values of 2.76, 4.26, 29.66, 18.86, and 10.21 μM, respectively. The antitumor activity of compound 5h was confirmed by a colony forming assay. Further, our results indicated that the antitumor activity of compound 5h may be mediated by enhancing expression of p21 and cl-caspase3, and leading to apoptosis of cancer cells.

Ligand-free Ullmann-type C-heteroatom couplings under practical conditions

A new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-type coupling reactions. This method allows the arylation of a wide range of amides, alcohols, and amines under practical conditions with bromobenzene and iodobenzene derivatives and will likely find direct application in current organic synthesis. The competitive reactivity among different functional groups is reported and rationalized, and the possibility to achieve selective arylation reactions is demonstrated. Copyright

N-arylbenzonitrilium ions. Photochemical generation and effect of substituents in the phenyl rings on lifetimes in water and reactivity with azide ion

Nitrilium ions Ar-C≡N+-Ar′ have been studied by laser flash photolysis in aqueous solutions containing 20% acetonitrile. The cations were generated by photoheterolysis of benzimidate esters Ar-CZ=N-Ar′ (Z = -OC6H4-4-CN) with 4-cyanophenoxide as the photochemical leaving group. Rate constants for the reaction with water (kw), azide ion (kaz) and hydroxide (kOH) were measured. The cation Ph-C≡N+-Ph is only 50-fold shorter lived in water compared to Ph-C≡N+-iPr (2); thus the effect of replacing an N-alkyl group with N-phenyl is modest. These two cations are also shown to have similar lifetimes to iminium analogs, e.g. Ph-CH=N+ (Me)-Ph. Thus, addition of water to analogous sp and sp2 hybridized systems occurs at a similar rate, and the increased steric access to the nitrilium plays at most a modest role. For the series where substituents in Ar′ were varied with Ar equal to phenyl, the Hammett plot for log kw correlated with σ, with ρ = - 1.4. For the series where Ar was varied, the data correlated much better with σ+, although ρ+ was only -0.6. This remarkably small effect of substituents in Ar constrasts with the effects seen in benzylic carbocations, but is consistent with the nitrilium structure, with most of the positive charge located on the nitrogen. Rate constant ratios kaz:kw, including the N-alkylnitrilium ion 2, are constant at ～104, with values of kaz well below the diffusion limit, even for the most reactive nitrilium ions. This is very different behaviour from that of carbocations and arylnitrenium ions of similar lifetimes in water. For these cations the rate constants kaz would be at or at least approaching the diffusion limit.