270260-33-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-(Pyridin-2-yloxy)benzonitrile is used as a building block in the synthesis of pharmaceuticals and agrochemicals. Its unique chemical structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Light-Emitting Diodes (OLEDs):
4-(Pyridin-2-yloxy)benzonitrile is used as an electron transport material in OLEDs due to its electron transport properties. This application can lead to the development of more efficient and longer-lasting OLED devices.
Used in Anti-Inflammatory and Anti-Tumor Applications:
4-(Pyridin-2-yloxy)benzonitrile has been investigated for its anti-inflammatory and anti-tumor activities. Its potential therapeutic effects make it a promising candidate for the development of new drugs to treat various inflammatory and neoplastic conditions.

InChI:InChI=1/C12H8N2O/c13-9-10-4-6-11(7-5-10)15-12-3-1-2-8-14-12/h1-8H

Upstream product

• 109-04-6 2-bromo-pyridine 
• 767-00-0 4-cyanophenol 
• 694-59-7 pyridine N-oxide 
• 109-09-1 2-chloropyridine 
• 98-98-6 2-Picolinic acid 

Downstream Products

• 1138698-17-5 (Z)-N'-hydroxy-4-(pyridin-2-yloxy)benzamidine 
• 100-47-0 benzonitrile 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 10282-31-2 4-morpholinobenzonitrile 

Relevant academic research and scientific papers

Discovery of a new palladacycle precatalyst and its applications to C-O coupling reactions between electron-deficient phenols and functionalized heteroaryl chlorides

A new palladacycle precatalyst (J009 PreCat) was designed and synthesized. The precatalyst dramatically improved the yield of a class of extremely challenging cross-coupling reactions between functionalized heteroaryl chlorides and electron-deficient phenols. The reactions are easy to set up, are tolerant of various functional groups, and allow quick access to electron-deficient, highly functionalized diaryl ether compounds.

Transition-Metal-Catalyzed Transformation of Sulfonates via S-O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether

The catalytic conversion of sulfonates, a versatile class of pharmaceutical intermediates, is usually based on C-O bond cleavage. In this paper, however, we discover a rare transformation of sulfonates via S-O bond cleavage catalyzed by transition metal, through which alkyl sulfonates could undergo an intramolecular desulfitative C-O coupling to form aryl alkyl ethers in the presence of a nickel catalyst. Meanwhile, aryl sulfonates perform similarly to give diaryl ethers catalyzed by a palladium complex. This transformation could tolerate a wide range of functionalities. Controlled experiments reveal that the 2-pyridyl group is necessary to promote the reaction as designed. Crossover experiments proved that this transformation might proceed partly in an intermolecular pathway.

Identification of an Oxalamide Ligand for Copper-Catalyzed C?O Couplings from a Pharmaceutical Compound Library

A typical pharmaceutical compound library is stocked with molecular diversity and could provide a platform for the discovery of new ligand structures. Herein, we describe the use of this approach in combination with high throughput screening to identify N,N’-bis(thiophene-2-ylmethyl)oxalamide as a ligand that is generally effective for copper-catalyzed C?O cross-couplings to prepare both biarylethers as well as phenols under mild conditions.

4-(Phenoxy) and 4-(benzyloxy)benzamides as potent and selective inhibitors of mono-ADP-ribosyltransferase PARP10/ARTD10

Human Diphtheria toxin-like ADP-ribosyltranferases (ARTD) 10 is an enzyme carrying out mono-ADP-ribosylation of a range of cellular proteins and affecting their activities. It shuttles between cytoplasm and nucleus and influences signaling events in both compartments, such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling and S phase DNA repair. Furthermore, overexpression of ARTD10 induces cell death. We recently reported on the discovery of a hit compound, OUL35 (compound 1), with 330 nM potency and remarkable selectivity towards ARTD10 over other enzymes in the human protein family. Here we aimed at establishing a structure-activity relationship of the OUL35 scaffold, by evaluating an array of 4-phenoxybenzamide derivatives. By exploring modifications on the linker between the aromatic rings, we identified also a 4-(benzyloxy)benzamide derivative, compound 32, which is potent (IC50 = 230 nM) and selective, and like OUL35 was able to rescue HeLa cells from ARTD10-induced cell death. Evaluation of an enlarged series of derivatives produced detailed knowledge on the structural requirements for ARTD10 inhibition and allowed the discovery of further tool compounds with submicromolar cellular potency that will help in understanding the roles of ARTD10 in biological systems.

Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis

Because diaryl ethers are present as an important motif in pharmaceuticals and natural products, extensive studies for the development of novel methods have been conducted. A conventional method for the construction of the diaryl ether moiety is the intermolecular cross-coupling reaction of aryl halides and phenols with a copper or palladium catalyst. We developed a catalytic decarbonylative etherification of aromatic esters using a palladium or nickel catalyst with our enabling diphosphine ligand to give the corresponding diaryl ethers. The present reaction can be conducted on gram scale in excellent yield. This reaction not only functions in an intramolecular setting but also allows for a cross-etherification using other phenols.

Mild addition of nucleophiles to pyridine-N-oxides

A general and facile one-pot procedure for the synthesis of 2-substituted pyridines from the corresponding pyridine-N-oxides and nucleophiles is presented as a mild alternative to SNAr chemistry. A variety of nucleophiles and heterocyclic-N-oxi

ANTIBACTERIAL COMPOUNDS AND METHODS OF USING SAME

Embodiments of the present invention provide novel antibacterials that target penicillin-binding proteins or other important cellular targets. Methods for inhibiting growth (reproduction, etc.) of bacteria using compounds described herein are also provided. Various embodiments exhibit activity against gram positive bacteria, such as certain strains of Entercoccus and Staphylococcus aureus.

ANTIBACTERIAL COMPOUNDS AND METHODS OF USING SAME

Embodiments of the present invention provide novel antibactehals that target penicillin-binding proteins or other important cellular targets. Methods for inhibiting growth (reproduction, etc.) of bacteria using compounds described herein are also provided. Various embodiments exhibit activity against gram positive bacteria, such as certain strains of Entercoccus and Staphylococcus aureus.