137045-30-8

Usage

Uses

Used in Pharmaceutical Industry:
3-FLUORO-4-BIPHENYLCARBOXYLIC ACID is used as an impurity in the production of Flurbiprofen (F598700), an anti-inflammatory drug that serves as an analgesic. It is specifically classified as Flurbiprofen impurity E, which is crucial for maintaining the quality and efficacy of the final drug product.

InChI:InChI=1/C13H9FO2/c14-12-8-10(6-7-11(12)13(15)16)9-4-2-1-3-5-9/h1-8H,(H,15,16)

Upstream product

• 124-38-9 carbon dioxide 
• 41604-19-7 1-bromo-3-fluoro-4-phenylbenzene 
• 584-08-7 potassium carbonate 
• 153556-42-4 4-bromo-3-fluorobenzoic acid 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1093214-80-2 4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]phenylmethanol 
• 1093214-81-3 2-fluorobiphenyl-4-carboxylic acid[hydroxyimino(4-hydroxymethylphenyl)methyl]amide 
• 1093214-90-4 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(piperidine-1-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester 
• 1093214-71-1 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethylpropanoyloxymethyl) ester 
• 1093212-96-4 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester 
• 1093214-94-8 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(morpholine-4-carbonyl)piperidine-4-carboxylic acid benzyl ester 
• 1093213-63-8 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid dibenzyl ester 
• 1093213-64-9 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester 
• 1093213-16-1 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(piperidine-1-ylcarbamoyl)piperidine-4-carboxylic acid 
• 1093212-64-6 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid (2,2-dimethylpropanoyloxymethyl) ester 
• 1093212-86-2 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid (3,3-dimethyl-2-oxobutyl) ester 
• 1093213-41-2 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(morpholine-4-carbonyl)piperidine-4-carboxylic acid 
• 1093214-95-9 4-chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Oxidative α-C-C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O2at Room Temperature via Iron Photocatalysis

The selective α-C-C bond cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C-C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical roles to enable the formation of highly reactive O radicals from alcohols and the consequent two α-C-C bond cleavages.

Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives

L-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds A33-A38 substituted with 4-phenyl group on dihydrooxazole ring exhibited excellent antifungal activities against C. albicans, C. tropicalis and C. krusei, with MIC values in the range of 0.03–0.25 μg/mL. In addition, the metabolic stability of compounds A33 and A34 in human liver microsomes in vitro was improved significantly, with the half-life greater than 145 min and the half-life of 59.1 min, respectively. Moreover, pharmacokinetic studies in SD rats showed that A33 exhibited favourable pharmacokinetic properties, with a bioavailability of 77.69%, and half-life (intravenous administration) of 9.35 h, indicating that A33 is worthy of further study.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.

Design, synthesis and evaluation of biphenyl imidazole analogues as potent antifungal agents

To further explore the structure activity relationships (SARs) of our previously discovered antifungal lead compound (1), a series of biphenyl imidazole analogues were designed, synthesized and evaluated for their in vitro antifungal activity. Many of the

Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives

A series of β-azole-phenylacetone derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible fungal infections and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against five susceptible strains and five fluconazole-resistant strains. Antifungal activity tests showed that most of the compounds exhibited excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03–1 μg/mL. Compounds with R1 = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1–8 μg/mL. Compounds with R1 = H or 2-F (such as 15a, 15o, 15p) displayed moderate to good antifungal activity against fluconazole-resistant strains 632, 901 and 904 with MIC values in the range of 0.125–4 μg/mL. Notably, 15o and 15ae exhibited antifungal activity against five susceptible strains and five fluconazole-resistant strains. Preliminary mechanistic studies showed that the potent antifungal activity of compound 15ae stemmed from inhibition of C. albicans CYP51. Compounds 15o, 15z and 15ae were nearly nontoxic to mammalian A549 cells.

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.

AMINO ACID COMPOUNDS

[Problem] To provide novel compounds that are S1P1 receptor agonists and exhibit an immunosuppressive activities by inducing lymphocyte sequestration in secondary lymphoid tissues. In addition, to provide a pharmaceutical agent which comprises the compounds as an effective component, in particular to provide a therapeutic and/or prophylactic agent for an autoimmune disease and the like. [Solving Means] Amino acid compounds that are represented by the following Formula (1) are provided

NOVEL DICARBOXYLIC ACID DERIVATIVES AS S1P1 RECEPTOR AGONISTS

The present invention relates to new compounds of formula (I) possessing agonistic activity at sphingosine-1 -phosphate (S1 P) receptors, their process of preparation and their use as immunosuppressive agents. The invention is also directed to pharmaceutical compositions containing these compounds and use of these compounds for treatment/prevention of immune mediated diseases and conditions or inflammatory diseases and conditions.