52565-56-7

Basic information

• Product Name: 4-PHENYLPYRIDINE-2-CARBOXYLIC ACID
• Synonyms: 4-PHENYLPYRIDINE-2-CARBOXYLIC ACID;4-PHENYLPICOLINIC ACID;4-PHENYL-2-PYRIDINECARBOXYLIC ACID;4-Phenylpyridine-2-carboxylicacid97%
• CAS NO: 52565-56-7
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• EINECS: 1806241-263-5
• Product Categories: Carboxylic Acids;Pyridines;Carboxylic Acids
• Mol File: 52565-56-7.mol

Chemical Properties

• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 198.7 °C
• Appearance: /
• Density: 1.241 g/cm³
• Vapor Pressure: 2.76E-07mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.98±0.50(Predicted)
• CAS DataBase Reference: 4-PHENYLPYRIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYLPYRIDINE-2-CARBOXYLIC ACID(52565-56-7)
• EPA Substance Registry System: 4-PHENYLPYRIDINE-2-CARBOXYLIC ACID(52565-56-7)

Safety Data

• Hazardous Substances Data: 52565-56-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylpyridine-2-carboxylic acid is utilized as a key building block in the synthesis of a range of pharmaceuticals and agrochemicals. Its incorporation into these compounds is crucial for enhancing their therapeutic effects and agricultural applications.
Used in Organic Synthesis:
In the realm of organic synthesis, 4-phenylpyridine-2-carboxylic acid serves as a valuable reagent for introducing the 4-pyridyl carboxylic acid group into various molecules. This modification can alter the chemical and biological properties of the target molecules, expanding their potential uses.
Used in Antibacterial and Antifungal Applications:
4-Phenylpyridine-2-carboxylic acid has been studied for its potential biological activities, including its antibacterial and antifungal properties. This makes it a promising candidate for the development of new antimicrobial agents to combat drug-resistant infections.

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

Upstream product

• 54151-74-5 2-bromo-4-phenylpyridine 
• 30766-03-1 4-bromo-2-picolinic acid 
• 98-80-6 phenylboronic acid 
• 1019927-13-9 1-oxy-4-phenyl-pyridine-2-carbonitrile 

Downstream Products

• 906089-68-7 4-phenyl-pyridine-2-carboxamide, N-[(1S,2R)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-hydroxypropyl] 
• 1397226-47-9 C₂₀H₁₇N₃O₂S 

Relevant articles and documents

QUINOLINE DERIVATIVES USEFUL AS TYROSINE KINASE INHIBITORS

Disclosed are imidazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure (I) and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein R1, X, Y1, Y2, Y3 and Z are as described herein. In certain embodiments, a compound disclosed herein inhibits a cellular TAM receptor, and can be used to treat disease mediated by or involving the TAM receptor family.

Design, synthesis and biological evaluation of phenylpicolinamide sorafenib derivatives as antitumor agents

Two series of phenylpicolinamide sorafenib derivatives (14a–k, 15a–k) were designed and synthesized. They were evaluated for IC50 values against three cancer cell lines (A549, Hela, and MCF-7) and VEGFR2/KDR, BRAF, and CRAF kinases. Fourteen target compounds showed moderate to excellent cytotoxicity activity against the different cancer cells with potency from the single-digit μM to nanomole range. What’s more, six of them were equal to more potent than sorafenib against one or more cell lines. Most of the compounds showed bad activity against VEGFR2/KDR, BRAF, or CRAF kinases. The most promising compound 15f showed strong antitumor activities against A549 and MCF-7 cell lines with IC50 values of 5.43 ± 0.74 and 0.62 ± 0.21 μM, which were 1.29–6.79-fold more active than sorafenib (6.53 ± 0.82, 4.21 ± 0.62 μM), respectively and it exhibited moderate IC50 (7.1 μM) than 14f (IC50 = 3.1 μM). Structure–activity relationships (SARs) and docking studies indicated that replacement of diarylurea of sorafenib with phenylpicolinamide moiety benefits to the activity. The position of aryl group and the substitutions of aryl group have a great influence on antitumor activity and selectivity. Small volume groups of aryl group such as (substituted) alkyl groups (–CH3, –CF3), halogen atoms (–F) were favorable to the cytotoxicity. Exact action mechanism of target compounds is not quite clear and further study will be carried out to identify the target in near future.

Rare aryl amide structure heterocyclic compound and its preparation method and application

The invention discloses a biaryl amide structure containing heterocyclopyrimidine compound as well as a geometrical isomer, a pharmaceutically acceptable salt, a hydrate, a solvate or a prodrug and a preparation method of the heterocyclopyrimidine compound. The biaryl amide structure containing heterocyclopyrimidine compound as well as the pharmaceutically acceptable salt, the hydrate or the solvate of the heterocyclopyrimidine compound are taken as active components and mixed with a pharmaceutically acceptable carrier or excipient for preparation of composition and clinically acceptable dosage forms. The invention further discloses applications of the compound to preparation of drugs for treating and/or preventing hyperplastic diseases, preparation of drugs for treating and/or preventing cancer and preparation of drugs for treating and/or preventing prostate cancer, lung cancer and liver cancer.

Synthesis, biological evaluation and docking studies of sorafenib derivatives N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-4(5)-phenylpicolinamides

Background: Sorafenib is an important VEGFR2/KDR inhibitor which is widely used for the treatment of cancer. Objective: In this paper, two series of sorafenib analogues N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-4- phenylpicolinamides(13a-k) and N-(3-fluoro-4-(pyridin-4-yloxy)phenyl)-5-phenylpicolinamides (14a-k) were designed and synthesized. Methods: Their structures were confirmed by various analytical methods, such as 1 H and 13 C NMR, m.p., MS, HRMS. All of them were evaluated for IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). Results: Eleven of the synthesized compounds showed moderate to excellent cytotoxicity activity against different cancer cells, whose potency from single-digit μM to nanomolar range. And five of them were equal to more potent than sorafenib against one or more cell lines. The most promising compound 14c showed excellent antitumor activities against PC-3 and MCF-7 cell lines with IC50 values of 2.62±1.07 μM and 1.14±0.92 μM, which were 1.15 to 2.75-fold more active than sorafenib (3.03±1.01 μM, 3.14±1.65 μM), respectively. Conclusion: Structure-activity relationships (SARs) and docking studies indicated that the replacement of diarylurea of sorafenib with phenylpicolinamide moiety benefited to the activity. The position of aryl group and the substituents of aryl group had a great influence on antitumor activity and selectivity. The aryl groups with the substitute of alkyl groups (-CH3), halogen atoms (-F,Cl) were favorable to the cytotoxicity. However, this series of compounds showed moderate activity against VEGFR2/KDR kinase. Mechanism of target compounds was not quite clear and further study will be carried out to identify the possible target.

Design, synthesis, and docking studies of phenylpicolinamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety as c-Met inhibitors

Four series of phenylpicolinamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety (12a-e, 13a-f, 14a-f and 15a-i) were designed, synthesized and evaluated for the IC50 values against three cancer cell lines (A549, PC-3 and MCF-7) and c-Met kinase. Five selected compounds (13b, 15b, 15d, 15e and 15f) were further evaluated for the activity against HepG2 and Hela cell lines. Eighteen of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 valuables in single-digit μM to nanomole range. Seven of them are equal to more active than positive control Foretinib against one or more cell lines. The most promising compound 15f showed superior activity to Foretinib, with the IC50 values of 1.04 ± 0.11 μM, 0.02 ± 0.01 μM and 9.11 ± 0.55 μM against A549, PC-3 and MCF-7 cell lines, which were 0.62 to 19.5 times more active than Foretinib (IC50 values: 0.64 ± 0.26 μM, 0.39 ± 0.11 μM, 9.47 ± 0.22 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that replacement of quinoline nucleus of the previous active compounds with 1H-pyrrolo[2,3-b]pyridine moiety maintained even improved the potent cytotoxic activity. The results suggested that the introduction of fluoro atoms to the aminophenoxy part of target compounds or the phenyl group of pyrimidine substituted on C-4 position was benefit for the activity.

LINCOMYCIN DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY

Novel lincomycin derivatives are disclosed. These lincomycin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against bacteria, including gram positive organisms, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

2-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone

The present invention is directed to certain piperidine, pyrrolidine, and hexahydro-1H-azepine compounds of the general structural formula: STR1 wherein R1, R3, R4, R5, A, W, X, Y, and n axe as defined herein. T

2-Pyridylcarboxamides which inhibit arachidonic acid release

2-Pyridylcarboxamides are provided having the structure STR1 wherein n is 1 to 10; R is hydrogen, lower alkyl, alkali metal or an amine salt; and R1 is C6 -C20 alkyl, C6 -C20 alkenyl, C6 to C20 alkoxy or phenyl. These compounds are useful as inhibitors of arachidonic acid release and as such are useful as antiallergy agents.