5728-33-6

Usage

Uses

It is used as an active pharmaceutical intermediate.

Upstream product

• 7383-90-6 3,4'-dimethylbiphenyl 
• 89900-94-7 methyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate 
• 93-58-3 benzoic acid methyl ester 
• 108-44-1 1-amino-3-methylbenzene 
• 591-17-3 meta-bromotoluene 
• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 134694-63-6 ethyl 3'-methyl-[1,1'-biphenyl]-4-carboxylate 
• 350792-94-8 (cyclohexyl)(difluoro)(3-methylphenyl)silane 
• 619-58-9 4-iodobenzoic acid 
• 17933-03-8 m-tolylboronic acid 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 350792-86-8 (dichloro)(cyclohexyl)(3-methylphenyl)silane 
• 586-76-5 4-Bromobenzoic acid 

Downstream Products

• 473717-55-4 (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(3'-methyl-[1,1'-biphenyl]-4-yl)-methanone 

Relevant academic research and scientific papers

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.

A Novel Biphenyl-based Chemotype of Retinoid X Receptor Ligands Enables Subtype and Heterodimer Preferences

The nuclear retinoid X receptors (RXRs) are key ligand sensing transcription factors that serve as universal nuclear receptor heterodimer partners and are thus involved in numerous physiological processes. Therapeutic targeting of RXRs holds high potential but available RXR activators suffer from limited safety. Selectivity for RXR subtypes or for certain RXR heterodimers are promising strategies for safer RXR modulation. Here, we report systematic structure-activity relationship studies on biphenyl carboxylates as new RXR ligand chemotype. We discovered specific structural modifications that enhance potency on RXRs, govern subtype preference, and vary modulation of different RXR heterodimers. Fusion of these structural motifs enabled specific tuning of subtype preferential profiles with markedly improved potency. Our results provide further evidence that RXR subtype selective ligands can be designed and present a novel chemotype of RXR modulators that can be tuned for subtype and heterodimer preferences.

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

Melamine and melamine-formaldehyde polymers as ligands for palladium and application to Suzuki-Miyaura cross-coupling reactions in sustainable solvents

The Suzuki-Miyaura cross-coupling reaction is a foundation stone of modern organic synthesis, as evidenced by its widespread use in the preparation of pharmaceuticals, agrochemicals, polymers, and other functional materials. With the prevalence of this venerable reaction in industrial synthesis, it is prudent to ensure its application adheres to the tenets of green chemistry. The introduction of cross-coupling catalysts that are active in sustainable solvents is therefore an important endeavor. In this report, a melamine-palladium complex is introduced as a versatile catalyst for the Suzuki-Miyaura cross-coupling reaction. This catalyst is soluble and active in both water and the renewable organic solvent ethyl lactate. The melamine-palladium catalyst can also be cross-linked by reaction with formaldehyde to generate an insoluble polymeric catalyst that can be recovered after the cross-coupling. The melamine-palladium system is inexpensive, easy to handle, bench-stable, and effective in catalysis in the presence of a variety of impurities (high cross-coupling yields were obtained in reactions run in unfiltered river water to illustrate this final point). Additionally, investigations reported herein revealed an intriguing relationship between catalytic efficiency and the base employed in the cross-coupling reaction. Implications for the mechanism of transmetalation in aqueous Suzuki-Miyaura cross-coupling reaction are discussed.

An improved protocol for ligandless Suzuki-Miyaura coupling in water

Using a reverse order of addition of reagents, PdCl2 and Pd(OAc)2 are efficient catalysts for the Suzuki-Miyaura reactions in water. The ligandless and mild conditions, the high stability of the catalytic system, short reaction time and good to excellent yields are important features of this protocol.

COMPOUNDS AND METHODS

This invention relates to substituted benzanilides which are modulators, agonists or antagonists, of the CCR5 receptor. In addition, this invention relates to the treatment and prevention of disease states mediated by CCR5, including, but not limited to,

Biphenyl vasopressin agonists

A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1-C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one

Solid phase cross-coupling reaction of aryl(halo)silanes with 4-iodobenzoic acid

Aryl(alkyl)(halo)silanes undergo facile and efficient palladium catalyzed cross-coupling reaction with iodobenzoic acid tethered to the Wang resin. Acid cleavage releases unsymmetrical biaryl carboxylic acids with high conversions, purities and yields.

Solid-phase cross-coupling reaction of aryl(fluoro)silanes with 4- iodobenzoic acid

Aryl(alkyl)(difluoro)silanes undergo a facile and efficient palladium- catalyzed cross-coupling reaction with iodobenzoic acid tethered to the Wang resin. Acid cleavage releases unsymmetrical biaryl carboxylic acids with high conversions, purities, and yields. (C) 2000 Elsevier Science Ltd.

Identification and initial structure-activity relationships of a novel class of nonpeptide inhibitors of blood coagulation factor Xa

The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized β-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted β-alanines was also developed.