503536-75-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyridinamine,5-(4-methoxyphenyl)-(9CI) is used as a key intermediate compound for the preparation of various pharmaceutical agents. Its application reason lies in its unique chemical structure, which allows for the development of novel therapeutics with potential benefits in treating different health conditions.
Used in Enzyme Inhibition:
In the field of biochemistry, 2-Pyridinamine,5-(4-methoxyphenyl)-(9CI) is utilized as a precursor in the synthesis of luciferase inhibitors. These inhibitors are essential tools for studying the function and regulation of luciferase enzymes, which are involved in various biological processes.
Used in Antifungal Applications:
2-Pyridinamine,5-(4-methoxyphenyl)-(9CI) is also used as a starting material for the development of substituted triazoles, which exhibit antifungal properties. These antifungal agents are crucial in combating fungal infections and can be used in the agricultural and medical industries to protect plants and treat human diseases.
Used in Metabolite Research:
Furthermore, 2-Pyridinamine,5-(4-methoxyphenyl)-(9CI) is employed in the synthesis of PhIP (A617000) metabolites and derivatives. PhIP is a heterocyclic amine found in cooked meat products and has been linked to various health concerns. The study of its metabolites and derivatives can provide valuable insights into the mechanisms of its action and potential mitigation strategies.

InChI:InChI=1/C12H12N2O/c1-15-11-5-2-9(3-6-11)10-4-7-12(13)14-8-10/h2-8H,1H3,(H2,13,14)

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1087036-68-7 N-[(3'-bromo-5'-(4''-methoxyphenyl))pyridin-2'-yl]pyridinium aminide 
• 504-29-0 2-aminopyridine 
• 20511-12-0 2-amino-5-iodopyridine 
• 1072-98-6 5-chloro-2-pyridylamine 

Downstream Products

• 96721-88-9 C₁₁H₁₀N₂O 
• 1044239-24-8 N-[5-(4-methoxyphenyl)pyridin-2-yl]benzamide 

Relevant academic research and scientific papers

Recyclable Pd/CuFe2O4 nanowires: A highly active catalyst for C-C couplings and synthesis of benzofuran derivatives

Pd/CuFe2O4 nanowire-catalyzed cross coupling transformations are described. Notably, these reactions showed excellent functional group tolerance. Further, the protocol is applied to a one-pot synthesis of benzofurans via a Sonogashira coupling and intramolecular etherification sequence. The catalyst was reused and found to maintain its activity and stability.

Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base

The Pd-catalyzed Suzuki coupling reactions of a series of aryl chlorides and aryl bromides containing basic nitrogen centers with arylboronic acids in water in the absence of added base are reported. The reactions proceed either partially or entirely under acidic conditions. After surveying twenty-two phosphorus ligands, high yields of products were obtained with aryl chlorides only when a bulky ligand, 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole (cataCXiumPtB) was used. In contrast, aryl bromides produced high yields of products in the absence of both added base and added ligand. In order to explore the Suzuki coupling process entirely under acidic conditions, a series of reactions were conducted in buffered acidic media using several model substrates. 4-Chlorobenzylamine, in the presence of cataCXiumPtB, produced high yields of product at buffered pH 6.0; the yields dropped off precipitously at buffered pH 5.0 and lower. The fall-off in yield was attributed to the decomposition of the Pd-ligand complex due to the protonation of the ligand in the more acidic aqueous media. In contrast, in the absence of an added ligand, 4-amino-2-chloropyridine produced quantitative yields at buffered pH 3.5 and 4.5 while 4-amino-2-bromopyridine produced quantitative yields in a series of buffered media ranging from pH 4.5 to 1.5. These substrates are only partially protonated in acidic media and can behave as active Pd ligands in the Suzuki catalytic cycle.

Synthesis and evaluation of the anticoccidial activity of trifluoropyrido[1,2-a]pyrimidin-2-one derivatives

Screening of our chemical library to discover new molecules exhibiting in vitro activity against the invasion of host cells by Eimeria tenella revealed a lead compound with an IC50 of 15 μM. Structure-activity relationship studies were conducted with 34 newly synthesized compounds to identify more active molecules and enhance in vitro activity against the parasite. Four compounds were more effective in inhibiting MDBK cell invasion in vitro than the lead compound.

An active, general, and long-lived palladium catalyst for cross-couplings of deactivated (hetero)aryl chlorides and bromides with arylboronic acids

An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp3)-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

A highly active catalytic system for Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water

An easily available Pd(OAc)2/(2-mesitylindenyl) dicyclohexylphosphine/Me(octyl)3N+Cl-/K 3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki-Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.

A new class of pyrazolopyridine nucleus with fluorescent properties, obtained through either a radical or a Pd arylation pathway from N-azinylpyridinium N-aminides

(Chemical Equation Presented) The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives - both of which incorporate a 3-aryl moiety - can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.

False positives in a reporter gene assay: Identification and synthesis of substituted N-pyridin-2-ylbenzamides as competitive inhibitors of firefly luciferase

Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay scre

Synthesis and SAR studies of biaryloxy-substituted triazoles as antifungal agents

A series of 1-(substituted biaryloxy)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl) propan-2-ol were synthesized and their antifungal activities were evaluated against eight human pathogenic fungi in vitro. Seventeen compounds showed activity 4- to 64-fold higher than voriconazole against Candida albicans. SAR clearly suggested that introduction of a biaryloxy side chain greatly enhanced the antifungal activity of triazole analogs against Candida species.

New 5-aryl pyridines as 11-beta inhibitors for the treatment of diabetes

Compounds of formula (I): as well as pharmaceutically acceptable salts and esters thereof used in the form of pharmaceutical compositions.