60277-38-5

Upstream product

• 125150-63-2 3-(4'-hydroxybiphenyl-4-yl)-propionic acid methyl ester 
• 1071836-09-3 methyl 3-(4'-methoxy-[1,1'-biphenyl]-4-yl)propanoate 

Downstream Products

• 60277-68-1 2-{4'-[2-(5-Chloro-2-methoxy-phenylcarbamoyl)-ethyl]-biphenyl-4-yloxy}-2-methyl-propionic acid ethyl ester 
• 60277-37-4 N-(5-Chloro-2-methoxy-phenyl)-3-(4'-hydroxy-biphenyl-4-yl)-propionamide 

Relevant academic research and scientific papers

Deconstruction as a strategy for the design of libraries of self-assembling dendrons

Bringing down the dendron: The deconstruction of self-assembling dendrons represents a new strategy for the rational design of libraries of self-assembling dendrons with unprecedented primary structure (see picture). In this strategy, molecular targets ar

Predicting the structure of supramolecular dendrimers via the analysis of libraries of AB3 and constitutional isomeric AB2 biphenylpropyl ether self-assembling dendrons

The synthesis of 4′-hydroxy-4-biphenylpropionic, 3′,4′- dihydroxy-4-biphenylpropionic, 3′,5′-dihydroxy-4-biphenylpropionic, and 3′,4′,5′-trihydroxy-4-biphenylpropionic methyl esters via three efficient and modular strategies including one based on Ni-catalyzed borylation and sequential cross-coupling is reported. These building blocks were employed in a convergent iterative approach to the synthesis of one library of 3,4,5-trisubstituted and two libraries of constitutional isomeric 3,4- and 3,5-disubstituted biphenylpropyl ether dendrons. Structural and retrostructural analysis of supramolecular dendrimers revealed that biphenylpropyl ether dendrons self-assemble and self-organize into the same periodic lattices and quasi-periodic arrays observed in previously reported libraries, but with larger dimensions, different mechanisms of self-assembly, and improved solubility, thermal, acidic, and oxidative stability. The different mechanisms of self-assembly led to the discovery of two new supramolecular structures. The first represents a new banana-like lamellar crystal with a four layer repeat. The second is a giant vesicular sphere self-assembled from 770 dendrons that exhibits an ultrahigh molar mass of 1.73 × 106 g/mol. Thus, the enhanced size of the self-assembled structures constructed from biphenylpropyl ether dendrons permitted for the first time discrimination of various molecular mechanisms of spherical self-assembly and elaborated a continuum between small filled spheres and very large hollow spheres that is dictated by the primary structure of the dendron. The comparative analysis of libraries of biphenylpropyl ether dendrons with the previously reported libraries of benzyl-, phenylpropyl-, and biphenyl-4-methyl ether dendrons demonstrated biomimetic self-assembly wherein the primary structure of the dendron and to a lesser extent the structure of its repeat unit determines the supramolecular tertiary structure. A "nanoperiodic table" of self-assembling dendrons and supramolecular dendrimers that allows the prediction of the general features of tertiary structures from primary structures was elaborated.

Design, synthesis, and evaluation of biphenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors

A series of hydroxamic acid-based histone deacetylase (HDAC) inhibitors were designed on the basis of a model of the HDAC2 binding site and synthesized. They are characterized by a cinnamic spacer, capped with a substituted phenyl group. Modifications of the spacer are also reported. In an in vitro assay with the isoenzyme HDAC2, a good correlation of the activity with the docking energy was found. In human ovarian carcinoma IGROV-1 cells, selected compounds produced significant acetylation of p53 and α-tubulin. Most compounds showed an antiproliferative activity comparable to that of SAHA. At equitoxic concentrations, the tested compounds were more effective than SAHA in inducing apoptotic cell death. Compounds selected for in vivo evaluation exhibited a significant antitumor activity on three tumor models at well tolerated doses, thus suggesting a good therapeutic index.

Biphenyloxy derivatives and antihyperlipidemic use

Compounds of the formula STR1 wherein R1 is straight or branched alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenylalkyl, phenylalkenyl, pyridyl or STR2 where X, Y and Z are each hydrogen, halogen, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms, R2 is hydrogen or alkyl of 1 to 4 carbon atoms, R3 is hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 7 carbon atoms or cycloalkoxycarbonyl or 4 to 8 carbon atoms, A is --CO--NH-- or --NH--CO--, and n is 1, 2 or 3, And, when R3 is carboxyl, non-toxic salts thereof formed with an inorganic or organic base; the compounds as well as the salts are useful as antihyperlipidemics.