28668-32-8

Basic information

• Product Name: 6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID
• Synonyms: 6-Phenylpyrimidine-4-carboxylicacid
• CAS NO: 28668-32-8
• Molecular Formula: C₁₁H₈N₂O₂
• Molecular Weight: 200.19
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 28668-32-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 173-177 °C(lit.)
• Boiling Point: 440.6oC at 760 mmHg
• Flash Point: 220.3oC
• Appearance: /
• Density: 1.302g/cm3
• Vapor Pressure: 1.54E-08mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID(28668-32-8)
• EPA Substance Registry System: 6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID(28668-32-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 28668-32-8(Hazardous Substances Data)

Usage

General Description

6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID is a chemical compound with a molecular formula C13H9N3O2. It belongs to the class of pyrimidinecarboxylic acids, with a phenyl group attached at the 6th position of the pyrimidine ring. 6-PHENYL-4-PYRIMIDINECARBOXYLIC ACID has potential applications in the pharmaceutical industry, as it has been studied for its potential therapeutic effects. Its molecular structure suggests that it may have biological activity and could be used as a building block in the synthesis of new pharmaceutical compounds. Additionally, it may also have other industrial applications, such as in the production of dyes or as a chemical intermediate in organic synthesis.

InChI:InChI=1/C11H8N2O2/c14-11(15)10-6-9(12-7-13-10)8-4-2-1-3-5-8/h1-7H,(H,14,15)

Upstream product

• 17759-27-2 4-methyl-6-phenylpyrimidine 
• 98-80-6 phenylboronic acid 
• 3435-26-5 4-chloro-6-phenylpyrimidine 
• 74647-38-4 6-phenylpyrimidine-4-carboxylic acid methyl ester 
• 98-86-2 acetophenone 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 3438-48-0 4-phenylpyrimidine 
• 28840-36-0 6-phenylpyrimidine-4-carboxamide 

Downstream Products

• 1311195-60-4 (6-phenylpyrimidin-4-yl)(3,4,5-trimethoxyphenyl)methanone 
• 1311195-92-2 N-methoxy-N-methyl-6-phenylpyrimidine-4-carboxamide 
• 1044873-08-6 N-(6-phenyl-4-pyrimidinoyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1044873-11-1 N-(6-phenyl-4-pyrimidinoyl)-5,6-dichloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 28840-36-0 6-phenylpyrimidine-4-carboxamide 
• 74502-99-1 N-methyl-6-phenylpyrimidine-4-carboxamide 
• 74503-00-7 N,N-dimethyl-6-phenylpyrimidine-4-carboxamide 
• 74502-98-0 (6-phenylpyrimidin-4-yl)methanol 
• 74647-32-8 ethyl 6-phenylpyrimidine-4-carboxylate 
• 74647-38-4 6-phenylpyrimidine-4-carboxylic acid methyl ester 

Relevant articles and documents

Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 μM) with no obvious cytotoxicity (CC50 > 50 μM). It effectively attenuated hypoxia-induced HIF-1α protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

Synthesis, activity and docking studies of phenylpyrimidine–carboxamide Sorafenib derivatives

Two series of Sorafenib derivatives bearing phenylpyrimidine–carboxamide moiety (16a–g and 17a–p) were designed, synthesized and evaluated for the IC50values against three cancer cell lines (A549, MCF-7 and PC-3). Two selected compounds (17f and 17n) were further evaluated for the activity against VEGFR2/KDR kinase. More than half of the synthesized compounds showed moderate to excellent activity against three cancer cell lines. Compound 17f showed equal activity to Sorafenib against MCF-7 cell line, with the IC50values of 6.35 ± 0.43 μM. Meanwhile, compound 17n revealed more active than Sorafenib against A549 cell line, with the IC50values of 3.39 ± 0.37 μM. Structure–activity relationships (SARs) and docking studies indicated that the second series (17a–p) showed more active than the first series (16a–g). What's more, the introduction of fluoro atom to the phenoxy part played no significant impact on activity. In addition, the presence of electron-donating on aryl group was benefit for the activity.

KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF

Certain chemical entities are provided herein. Also provided are pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.