4-Biphenylcarboxylic acid

A New Structural Family of Gas-Sorbing Coordination Polymers Derived from Phenolic Carboxylic Acids.[Pubmed:26525776]

Chemistry. 2015 Dec 7;21(50):18057-61.

The structure of Li(inox)2/3 DMF (inox(-) =the N-oxide of the isonicotinate anion) consists of a 3D framework with solvent-filled, square cross-section channels of approximate dimensions 5.5x5.5 A. Unfortunately, the Li(inox) framework is unstable upon removal of DMF from the channels. When the structurally related 4-hydroxybenzoic acid (H2 hba) was used in place of Hinox, and Zn(2+) in place of the Li(+) , a structurally similar but more robust network, Zn(hba), was obtained; the isostructural compound, Co(hba), may also be prepared. Longer ligands with phenolate and carboxylate functional groups at opposite ends, such as the dianions of 4-coumaric acid (H2 cma) and 4'-hydroxy-4-Biphenylcarboxylic acid (H2 hbpc), in combination with Zn(2+) yield Zn(cma) and Zn(hbpc) frameworks, respectively, with the same PtS topology but with larger channels. The coordination polymers remain intact after desolvation and exhibit microporosity, showing the ability to sorb significant quantities of CO2 , CH4 , and H2 .

Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands.[Pubmed:19239230]

J Med Chem. 2009 Mar 26;52(6):1540-5.

We recently discovered the isoform selective RAR beta 2 ligand 4'-octyl-4-Biphenylcarboxylic acid (3, AC-55649). Although 3 is highly potent at RAR beta 2 and displays excellent selectivity, solubility issues make it unsuitable for drug development. Herein we describe the exploration of the SAR in a biphenyl and a phenylthiazole series of analogues of 3. This ultimately led to the design of 28, a novel, orally available ligand with excellent isoform selectivity for the RAR beta 2.

Triplet excited fluoroquinolones as mediators for thymine cyclobutane dimer formation in DNA.[Pubmed:17523621]

J Phys Chem B. 2007 Jun 28;111(25):7409-14.

A series of fluoroquinolones (FQs), including enoxacin (ENX), pefloxacin (PFX), norfloxacin (NFX), its N(4')-acetyl derivative (ANFX), ofloxacin (OFX), and rufloxacin (RFX) have been investigated to determine their potential as DNA photosensitizers via thymine cyclobutane dimer (T

Discovery of a potent, orally available, and isoform-selective retinoic acid beta2 receptor agonist.[Pubmed:16302793]

J Med Chem. 2005 Dec 1;48(24):7517-9.

T) formation in DNA. At fluoroquinolone concentrations and light doses insufficient to produce direct single strand breaks, ENX, PFX, and NFX were able to produce T

Palladium(II)-catalyzed sequential hydroxylation-carboxylation of biphenyl using formic acid as a carbonyl source.[Pubmed:15228298]

Org Lett. 2004 Jul 8;6(14):2437-9.

T dimers in DNA, revealed by enzymatic treatment with T4 endonuclease V. By contrast, ANFX, OFX, and RFX were inefficient in this assay. The absolute values of the triplet energies of ENX, PFX, NFX, ANFX, OFX, and RFX were estimated by means of laser flash photolysis, using flurbiprofen, 4-Biphenylcarboxylic acid, and naproxen as energy acceptors. They were found to be 273, 269, 269, 265, 262, and 253 kJ/mol, respectively. Other triplet excited state properties of the FQs, including quantum yields and lifetimes, were also studied. All the results indicate that the threshold ET value required for a given compound to become a potential DNA photosensitizer via T

Thermochemistry of biphenylcarboxylic and dicarboxylic acids. A combined experimental and theoretical study.[Pubmed:15105925]

Org Biomol Chem. 2004 May 7;2(9):1353-8.

T formation is in the range defined by the triplet energies of NFX and ANFX (265-269 kJ/mol). This provides the basis for an alert rule: any chemical (drugs, cosmetics, pesticides, etc.) with higher ET has to be considered with regard to its potential photogenotoxicity.

Effects of amino acids on the amidation of polyaromatic carboxylic acids by Bacillus cereus.[Pubmed:11577715]

Biosci Biotechnol Biochem. 2001 Aug;65(8):1761-5.

4'-Octyl-4-Biphenylcarboxylic acid (1g, AC-55649) was identified as a highly isoform-selective agonist at the human RARbeta2 receptor in a functional intact cell-based screening assay. The subsequent hit to lead optimization transformed the lipophilic, poorly soluble hit into a more potent and orally available compound (2, AC-261066) with retained beta2 selectivity and greatly improved physiochemical properties. Being an isoform-selective RARbeta2 receptor agonist that discriminates between nuclear receptor isoforms having identical ligand binding domains, 2 will be useful as a pharmacological research tool but also a valuable starting point for drug development.

Effects of steric bulk and conformational rigidity on fatty acid omega hydroxylation by a cytochrome P450 4A1 fusion protein.[Pubmed:8837739]

Arch Biochem Biophys. 1996 Oct 1;334(1):59-66.

[reaction: see text] A simultaneous hydroxylation-carboxylation of biphenyl occurred to give 4'-hydroxy-4-Biphenylcarboxylic acid, which has wide potential application as a polyester monomer.

Possible intermolecular interaction between quinolones and biphenylacetic acid inhibits gamma-aminobutyric acid receptor sites.[Pubmed:7840564]

Antimicrob Agents Chemother. 1994 Oct;38(10):2323-9.

The standard molar enthalpies of combustion and sublimation of 2- and 4-Biphenylcarboxylic acid, 2,2'- and 4,4'-biphenyldicarboxylic acid were measured and the gas-phase enthalpies of formation, at T= 298.15 K, were determined. Ab initio calculations were performed and a theoretical study on molecular structure of all the biphenyl acid isomers has been carried out. Calculated enthalpies of formation using appropriate isodesmic reactions are compared with experimental values, and a good agreement is observed. Estimates of enthalpies of formation for the isomers, which were not studied experimentally, are presented. All the acids containing at least one ortho COOH are comparatively less stable than their isomers having just meta or para COOH group(s).

Effects of some antitumor agents on growth and glycolytic enzymes of the flagellate Crithidia.[Pubmed:5781578]

J Bacteriol. 1969 Apr;98(1):23-8.

The soil bacterium Bacillus cereus Tim-r01 efficiently transformed polyaromatic carboxylic acids (PACA) such as 4-Biphenylcarboxylic acid (4-BPCA), 4-biphenylacetic acid, and 4-phenoxybenzoic acid into their corresponding amides. The amidation activity was expressed at 37 degrees C (pH 7-8) in the presence of grown cells in nutrients under an aerobic atmosphere. Other strains of B. cereus, IFO 3001 and IAM 1229, also gave the amide from 4-BPCA. In phosphate-buffered saline (PBS), the addition of normal amino acids was essential, while sulfur-containing amino acids such as methionine and cysteine drastically inhibited the amidation. Tracer experiments using N-15-isoleucine and N-15-alanine showed that the nitrogen atom of the amide came from an amino group of amino acids but not from ammonia or alkylamines.