135613-33-1Relevant articles and documents
Discovery and optimization of a biphenylacetic acid series of prostaglandin D2 receptor DP2 antagonists with efficacy in a murine model of allergic rhinitis
Scott, Jill M.,Baccei, Christopher,Bain, Gretchen,Broadhead, Alex,Evans, Jilly F.,Fagan, Patrick,Hutchinson, John H.,King, Christopher,Lorrain, Daniel S.,Lee, Catherine,Prasit, Peppi,Prodanovich, Pat,Santini, Angelina,Santini, Brian A.
scheme or table, p. 6608 - 6612 (2011/12/04)
Biphenylacetic acid (5) was identified through a library screen as an inhibitor of the prostaglandin D2 receptor DP2 (CRTH2). Optimization for potency and pharmacokinetic properties led to a series of selective CRTH2 antagonists. Compounds demonstrated potency in a human DP2 binding assay and a human whole blood eosinophil shape change assay, as well as good oral bioavailability in rat and dog, and efficacy in a mouse model of allergic rhinitis following oral dosing.
3-arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal
Battistuzzi, Gianfranco,Cacchi, Sandro,Fabrizi, Giancarlo,Bernini, Roberta
, p. 1133 - 1136 (2007/10/03)
The reaction of aryl halides with acrolein diethyl acetal in the presence of Pd(OAc)2, n-Bu3N, and n-Bu4NCl in DMF at 90°C affords ethyl 3-arylpropanoates. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, nitrile, and nitro groups. ortho-Substituents do not hamper the reaction. 3-Arylpropanoate esters were isolated in good to excellent yields with many neutral, electron-rich and electron-poor aryl iodides and electron-poor aryl bromide. Neutral and electron-rich aryl bromides gave the desired ester in moderate yields.
Synthesis and hydrogen bonding capabilities of biphenyl-based amino acids designed to nucleate β-sheet structure
Nesloney, Carey L.,Kelly, Jeffery W.
, p. 3127 - 3137 (2007/10/03)
The syntheses of 3′-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3′-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate β-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the β-turn. N-Benzyl-3′-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3′-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.
BIPHENYL OXADIAZINONE ANGIOTENSIN II INHIBITORS
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, (2008/06/13)
Angiotension II inhibition is exhibited by STR1 wherein: R. sup.1 and R 2 are each independently hydrogen, alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, thiophenalkyl, pyridylalkyl, or--R 8 CO. sub.2 R 9 ;R 3 is a single bond,--S--, or--O--;
