115444-30-9

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 1424-22-2 1-cyclohexenyl acetate 
• 70644-46-1 4-(3-cyclohexen-1-yl)pyridine 
• 1120-87-2 4-bromopyridin 
• 930-68-7 cyclohexenone 
• 1692-15-5 4-pyridylboronic acid 
• 181219-01-2 4-pyridineboronic acid pinacol ester 
• 1104636-72-7 4-pyridylboronic acid MIDA ester 
• 4969-01-1 1,4-dioxaspiro[4.5]decan-7-one 

Downstream Products

• 117960-61-9 2-acetyl-5-(4-pyridyl)cyclohexanone 

Relevant academic research and scientific papers

Discovery of a First-in-Class Inhibitor of the Histone Methyltransferase SETD2 Suitable for Preclinical Studies

SET domain-containing protein 2 (SETD2), a histone methyltransferase, has been identified as a target of interest in certain hematological malignancies, including multiple myeloma. This account details the discovery of EPZ-719, a novel and potent SETD2 inhibitor with a high selectivity over other histone methyltransferases. A screening campaign of the Epizyme proprietary histone methyltransferase-biased library identified potential leads based on a 2-amidoindole core. Structure-based drug design (SBDD) and drug metabolism/pharmacokinetics (DMPK) optimization resulted in EPZ-719, an attractive tool compound for the interrogation of SETD2 biology that enables in vivo target validation studies.

1,4-Addition of aryl boronic acids to α,β-unsaturated ketones catalyzed by a CCC-NHC pincer rhodium complex

An air- and water-stable CCC-NHC pincer Rh complex catalyzed the 1,4-addition of aryl boronic acids to α,β-unsaturated ketones and aldehydes. This bench top method proceeds in eco-friendly solvents including methanol and water. The scope of boronic acids was expanded to include heterocyclic examples.

Electroreductive 4-Pyridylation of Electron-deficient Alkenes with Assistance of Ni(acac)2

An electroreductive 4-pyridylation of activated alkenes was developed in an undivided cell with the assistance of Ni(acac)2 (acac = acetylacetone). This novel protocol is compatible with a broad range of electron-poor alkenes, which are commonl

Metal-Free Synthesis of C-4 Substituted Pyridine Derivatives Using Pyridine-boryl Radicals via a Radical Addition/Coupling Mechanism: A Combined Computational and Experimental Study

Density functional theory investigations revealed that the pyridine-boryl radical generated in situ using 4-cyanopyridine and bis(pinacolato)diboron could be used as a bifunctional “reagent”, which serves as not only a pyridine precursor but also a boryl radical. With the unique reactivity of such radicals, 4-substituted pyridine derivatives could be synthesized using α,β-unsaturated ketones and 4-cyanopyridine via a novel radical addition/C-C coupling mechanism. Several controlled experiments were conducted to provide supportive evidence for the proposed mechanism. In addition to enones, the scope could be extended to a wide range of boryl radical acceptors, including various aldehydes and ketones, aryl imines and alkynones. Lastly, this transformation was applied in the late-stage modification of a complicated pharmaceutical molecule.

Heteroarylboronates in rhodium-catalyzed 1,4-addition to enones

Rhodium(I)-catalyzed 1,4-addition of aryl and alkenylboronic acids to α,β-unsaturated carbonyl compounds is well established, but the transfer of heteroaryl residues in this reaction remains underdeveloped. We have studied heteroaryl MIDA and pinacol boro

Liquid phase oxidation of alkenes with nitrous oxide to carbonyl compounds

A variety of substrates including linear, cyclic, heterocyclic alkenes and their derivatives were tested in the liquid phase non-catalytic oxidation with nitrous oxide (N2O). The structure and composition of the alkenes have a significant effect on the reaction selectivity. With many alkenes, N 2O oxidation provides a selective way for the preparation of carbonyl compounds. The generation of carbene (or diazomethane) species is a remarkable feature of the oxidation of terminal alkenes.

Cardiotonic Agents. 1-Methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinones and Related Compounds. Synthesis and Activity

A series of 1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinones and related compounds were synthesized and evaluated for positive inotropic activity.Most members of this series exerted a dose-dependent increase in myocardial contractility in the dog acute heart failure model, whereas they caused only slight changes in heart rate and blood pressure.Several derivatives, especially those with cyano, acetyl, and ethyl substituents at the 4-position, were more potent than milrinone, which was used as a reference. 4-Acetyl-1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinone (MS-857) is one of the most potent positive inotropic agents in this series.

REGIOCHEMICAL CONTROL IN THE ALLYLIC HYDROGEN ABSTRACTION FROM 1-X-SUBSTITUTED CYCLOHEXENES

Allylic hydrogen abstraction is strongly affected by substituents attached to the double bond.Evidence regarding this regiochemical control is presented for the first time.