55240-51-2

Basic information

• Product Name: 2-PHENYL-ISONICOTINIC ACID
• Synonyms: 2-PHENYLPYRIDINE-4-CARBOXYLIC ACID;2-PHENYL-ISONICOTINIC ACID;2-Phenyl-4-pyridinecarboxylic acid;2-Phenylpyridine-4-carboxylic acid, 4-Carboxy-2-phenylpyridine
• CAS NO: 55240-51-2
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• EINECS: 200-258-5
• Product Categories: Carboxylic Acids;Pyridines;API intermediates;Carboxylic Acids
• Mol File: 55240-51-2.mol

Chemical Properties

• Melting Point: 270-271 °C
• Boiling Point: 478.8 °C at 760 mmHg
• Flash Point: 243.4 °C
• Appearance: /
• Density: 1.241g/cm³
• Vapor Pressure: 5.6E-10mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.89±0.10(Predicted)
• CAS DataBase Reference: 2-PHENYL-ISONICOTINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-ISONICOTINIC ACID(55240-51-2)
• EPA Substance Registry System: 2-PHENYL-ISONICOTINIC ACID(55240-51-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 55240-51-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyl-isonicotinic acid is used as a building block for the synthesis of various drugs and biologically active molecules. Its unique structure allows for the development of new compounds with therapeutic potential.
Used in Medicinal Chemistry Research:
2-Phenyl-isonicotinic acid is used as a starting material for the design and synthesis of novel compounds with potential anti-tumor and anti-inflammatory properties. Its ability to modulate biological pathways makes it a valuable tool in the discovery of new therapeutic agents.
Used in Drug Discovery:
2-Phenyl-isonicotinic acid is used as a lead compound in drug discovery efforts, providing a foundation for the development of new pharmaceuticals with improved efficacy and safety profiles.

InChI:InChI=1/C12H9NO2/c14-12(15)10-6-7-13-11(8-10)9-4-2-1-3-5-9/h1-8H,(H,14,15)

Upstream product

• 33252-30-1 2-chloro-4-pyridinenitrile 
• 33744-17-1 2-phenylpyridine-4-carbonitrile 
• 98-80-6 phenylboronic acid 
• 4634-14-4 2-phenylisonicotinic acid methyl ester 
• 66572-56-3 2-bromoisonicotinic acid 
• 3475-21-6 4-methyl-2-phenylpyridine 

Downstream Products

• 58481-06-4 2-phenylisonicotinohydrazide 
• 1448440-56-9 (S)-N-(2-(2-cyanopyrrolidin-1-yl)-2-oxoethyl)-2-phenylisonicotinamide 
• 1416048-47-9 C₉₁H₁₄₃N₁₇O₂₃ 
• 1430330-70-3 N-(1,1-dioxo-1H-1λ⁶-benzo[b]thiophen-6-yl)-2-phenyl-isonicotinamide 
• 1359858-38-0 C₂₀H₁₇N₃O₂S 
• 4634-12-2 4-(hydroxymethyl)-2-phenylpyridine 
• 4634-14-4 2-phenylisonicotinic acid methyl ester 

Relevant articles and documents

Structure-Activity Relationship for the Picolinamide Antibacterials that Selectively Target Clostridioides difficile

Clostridioides difficile is a leading health threat. This pathogen initiates intestinal infections during gut microbiota dysbiosis caused by oral administration of antibiotics. C. difficile is difficult to eradicate due to its ability to form spores, which are not susceptible to antibiotics. To address the urgent need for treating recurrent C. difficile infection, antibiotics that selectively target C. difficile over common gut microbiota are needed. We herein describe the class of picolinamide antibacterials which show potent and selective activity against C. difficile. The structure-activity relationship of 108 analogues of isonicotinamide 4, a compound that is equally active against methicillin-resistant Staphylococcus aureus and C. difficile, was investigated. Introduction of the picolinamide core as exemplified by analogue 87 resulted in exquisite potency and selectivity against C. difficile. The ability of the picolinamide class to selectively target C. difficile and to prevent gut dysbiosis holds promise for the treatment of recurrent C. difficile infection.

Start Selective and Rigidify: The Discovery Path toward a Next Generation of EGFR Tyrosine Kinase Inhibitors

The epidermal growth factor receptor (EGFR), when carrying an activating mutation like del19 or L858R, acts as an oncogenic driver in a subset of lung tumors. While tumor responses to tyrosine kinase inhibitors (TKIs) are accompanied by marked tumor shrinkage, the response is usually not durable. Most patients relapse within two years of therapy often due to acquisition of an additional mutation in EGFR kinase domain that confers resistance to TKIs. Crucially, oncogenic EGFR harboring both resistance mutations, T790M and C797S, can no longer be inhibited by currently approved EGFR TKIs. Here, we describe the discovery of BI-4020, which is a noncovalent, wild-type EGFR sparing, macrocyclic TKI. BI-4020 potently inhibits the above-described EGFR variants and induces tumor regressions in a cross-resistant EGFRdel19 T790M C797S xenograft model. Key was the identification of a highly selective but moderately potent benzimidazole followed by complete rigidification of the molecule through macrocyclization.

Discovery of benzoylsulfonohydrazides as potent inhibitors of the histone acetyltransferase KAT6A

A high-throughput screen for inhibitors of the histone acetyltransferase, KAT6A, led to identification of an aryl sulfonohydrazide derivative (CTX-0124143) that inhibited KAT6A with an IC50 of 1.0 μM. Elaboration of the structure-activity relationship and medicinal chemistry optimization led to the discovery of WM-8014 (97), a highly potent inhibitor of KAT6A (IC50 = 0.008 μM). WM-8014 competes with acetyl-CoA (Ac-CoA), and X-ray crystallographic analysis demonstrated binding to the Ac-CoA binding site. Through inhibition of KAT6A activity, WM-8014 induces cellular senescence and represents a unique pharmacological tool.

Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen

Direct arylations of pyridines are challenging transformations due to the high Lewis basicity of the sp2-nitrogen. The use of carboxylates as directing groups is reported, facilitating the Pd-catalyzed C-H arylation of this difficult class of substrates. This methodology allows regioselective C3/C4 arylation, without the need to use solvent quantities of the pyridine, and using low-cost chloro- and bromoarenes as coupling partners. Furthermore, carboxylates could be employed as traceless directing groups through a one-pot C-H arylation/Cu(I)-mediated decarboxylation sequence, thereby accessing directing-group-free pyridine biaryls.

NOVEL FAP INHIBITORS

The present invention relates to novel inhibitors having high selectivity and specificity for FAP (fibroblast activation protein). Said inhibitors are useful as a human and/or veterinary medicine, in particular for the treatment and/or prevention of FAP-related disorders such as but not limited to proliferative disorders.

Extended structure-activity relationship and pharmacokinetic investigation of (4-quinolinoyl)glycyl-2-cyanopyrrolidine inhibitors of fibroblast activation protein (FAP)

Fibroblast activation protein (FAP) is a serine protease related to dipeptidyl peptidase IV (DPPIV). It has been convincingly linked to multiple disease states involving remodeling of the extracellular matrix. FAP inhibition is investigated as a therapeutic option for several of these diseases, with most attention so far devoted to oncology applications. We previously discovered the N-4-quinolinoyl-Gly-(2S)-cyanoPro scaffold as a possible entry to highly potent and selective FAP inhibitors. In the present study, we explore in detail the structure-activity relationship around this core scaffold. We report extensively optimized compounds that display low nanomolar inhibitory potency and high selectivity against the related dipeptidyl peptidases (DPPs) DPPIV, DPP9, DPPII, and prolyl oligopeptidase (PREP) the log D values, plasma stabilities, and microsomal stabilities of selected compounds were found to be highly satisfactory. Pharmacokinetic evaluation in mice of selected inhibitors demonstrated high oral bioavailability, plasma half-life, and the potential to selectively and completely inhibit FAP in vivo.

NOVEL FAP INHIBITORS

The present invention relates to novel inhibitors having high selectivity and specificity for FAP (fibroblast activation protein). Said inhibitors are useful as a human and/or veterinary medicine, in particular for the treatment and/or prevention of FAP-related disorders such as but not limited to proliferative disorders.

Synthesis and properties of a dendritic FRET donor-acceptor system with cationic iridium(iii) complex core and carbazolyl periphery

In order to enhance the photoluminescence of cyclometalated iridium(iii) complexes, which are potentially useful for biolabeling and bioimaging, a series of benzyl ether branched dendritic moieties with carbazolyl termini were introduced to the cyclometal

CYCLOMETALATED DYE COMPLEXES AND THEIR USE IN DYE-SENSITIZED SOLAR CELLS

The present invention provides a modular approach to preparing a large array of substituted cyclometalated compounds which behave as dyes having intense absorbance bands in the visible spectrum The compounds include at least one terpyridine-type ligand (tpy) and one cyclometalated tridentate ligand having the bonding motif N,C,N' or C,N, N'. In particular, compounds of formula (I) and formula (II), as shown, where M and R1 to R4 are as defined herein, are disclosed The utility of these compounds in dye-sensitized solar cells (DSSCs) is also taught.

SIRTUIN MODULATING COMPOUNDS

Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin- modulating compound in combination with another therapeutic agent.