18714-17-5

Basic information

• Product Name: 4-Phenylpyridine-2-carboxylic acid methyl ester
• Synonyms: 4-Phenylpyridine-2-carboxylic acid methyl ester;Methyl 4-phenylpicolinate
• CAS NO: 18714-17-5
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23194
• Mol File: 18714-17-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Phenylpyridine-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylpyridine-2-carboxylic acid methyl ester(18714-17-5)
• EPA Substance Registry System: 4-Phenylpyridine-2-carboxylic acid methyl ester(18714-17-5)

Safety Data

• Hazardous Substances Data: 18714-17-5(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 151503-15-0 C₂₂H₂₀NO₂P 
• 29681-42-3 methyl 4-bromopyridine-2-carboxylate 
• 98-80-6 phenylboronic acid 
• 768-03-6 Phenyl vinyl ketone 
• 821796-68-3 phenyl(1-tosylaziridin-2-yl)methanone 
• 585529-12-0 2-(1-phenylvinyl)-N-tosylaziridine 
• 683-98-7 methyl bromodifluoroacetate 
• 107969-78-8 methyl 4-phenyl-2-oxo-3-butenoate 
• 75-07-0 acetaldehyde 
• 107969-78-8 methyl benzylidenepyruvate 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 5470-22-4 4-chloropicolinic acid 
• 98-98-6 2-Picolinic acid 

Downstream Products

• 55218-73-0 2-(hydroxymethyl)-4-phenylpyridine 
• 261777-31-5 C₁₇H₂₃NO₄ 
• 261777-31-5 C₁₇H₂₃NO₄ 
• 1073461-87-6 N-((3S)-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-chromen-3-yl)-4-phenylpyridine-2-carboxamide 

Relevant articles and documents

Discovery of 4-Phenylpiperidine-2-Carboxamide Analogues as Serotonin 5-HT2CReceptor-Positive Allosteric Modulators with Enhanced Drug-like Properties

Targeting the serotonin (5-HT) 5-HT2C receptor (5-HT2CR) allosteric site to potentiate endogenous 5-HT tone may provide novel therapeutics to alleviate the impact of costly, chronic diseases such as obesity and substance use disorders. Expanding upon our recently described 5-HT2CR-positive allosteric modulators (PAMs) based on the 4-alkylpiperidine-2-carboxamide scaffold, we optimized the undecyl moiety at the 4-position with variations of cyclohexyl- or phenyl-containing fragments to reduce rotatable bonds and lipophilicity. Compound 12 (CTW0415) was discovered as a 5-HT2CR PAM with improved pharmacokinetics and reduced off-target interactions relative to our previous series of molecules. The in vivo efficacy of compound 12 to potentiate the effects of a selective 5-HT2CR agonist was established in a drug discrimination assay. Thus, 12 is reported as a 5-HT2CR PAM with characteristics suitable for in vivo pharmacological studies to further probe the biological and behavioral mechanisms of allosteric modulation of a receptor important in several chronic diseases.

Design, Synthesis, and Characterization of 4-Undecylpiperidine-2-carboxamides as Positive Allosteric Modulators of the Serotonin (5-HT) 5-HT2C Receptor

An impaired signaling capacity of the serotonin (5-HT) 5-HT2C receptor (5-HT2CR) has been implicated in the neurobehavioral processes that promote relapse vulnerability in cocaine use disorder (CUD). Restoration of the diminished 5-HT2CR signaling through positive allosteric modulation presents a novel therapeutic approach. Several new molecules with the 4-alkylpiperidine-2-carboxamide scaffold were designed, synthesized, and pharmacologically evaluated, leading to the discovery of selective 5-HT2CR positive allosteric modulators (PAMs). Compound 16 (CYD-1-79) potentiated 5-HT-evoked intracellular calcium release in cells stably expressing the human 5-HT2CR but not the 5-HT2AR cells. A topographically distinct allosteric site was identified based on the newly solved 5-HT2CR structure. Compound 16 modulated 5-HT2CR-mediated spontaneous ambulation, partially substituted for the training dose of the 5-HT2CR agonist WAY163909, synergized with a low dose of WAY163909 to substitute fully for the stimulus effects of WAY163909, and attenuated relapse vulnerability as assessed in a rodent self-administration model, indicating its therapeutic promise for CUD.

SMALL MOLECULE CORRECTORS OF MAMMALIAN SLC6A8 FUNCTION

Disclosed are compounds, compositions, and methods useful for treating or preventing a disease or disorder associated with mutation in a protein.

Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N-Tosyl Vinylaziridines with Difluoroalkyl Halides

A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6πelectrocyclization, and defluorinated aromatization.

Allosteric modulators of 5-hydroxytryptamine 2C receptor (5-HT2CR)

The disclosure is directed to compounds identified as allosteric modulators of 5-HT 2CR, as well as pharmaceutical compositions and methods using the same. Certain embodiments also include methods of identifying and methods of synthesizing the compounds. Optimization and development of allosteric 5-HT 2CR modulators that bind sites other than the primary ligand binding site generate novel, highly selective, and potent ligands of 5-HT2CR. Such molecules can be used as small molecule probes for the nervous system and as effective therapeutics for a variety of diseases.

Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines

An iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines in one step has been developed through the green reaction system of catalytic amounts of molecular iodine and amine in combination with oxyg

A mild and facile synthesis of polyfunctionalized pyridines: Merging three-component cyclization and aerobic oxidation by amine/metal catalysts

A mild and facile synthesis of polyfunctionalized pyridines from NH4OAc, β,γ-unsaturated α-ketoesters, and ketones/aldehydes has been reported through tandem three-component cyclization and aerobic oxidation using the combination of amine and m

Scope and limitation for FeSO4-mediated direct arylation of heteroarenes with arylboronic acids and its synthetic applications

FeSO4-mediated direct arylation of heteroarenes with arylboronic acids in the presence of K2S2O8 has been developed. A slow addition of an aqueous solution of an iron complex was crucial in the arylation. Scope and limitation of the heteroarenes and arylboronic acids are discussed. Furthermore, the direct arylation was applied to the formal total synthesis botryllazine B and sodium channel inhibitor.

A modular approach toward the synthesis of 2,4-disubstituted pyridines

A number of 2,4-disubstituted pyridines have been synthesized using α,β,γ,δ-unsaturated aldehydes and ammonium chloride in the presence of triethylamine in acetonitrile solvent at 80 C under air balloon.

ALLOSTERIC MODULATORS OF 5-HYDROXYTRYPTAMINE 2C RECEPTOR (5-HT2CR)

[000166] Embodiments of the invention are directed to methods of identifying, methods of synthesizing, and compositions identified as allosteric modulators of 5-HT2cR.