1022090-86-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Methylquinoline-6-boronic acid pinacol ester is used as a reactant in the synthesis of 1H-pyrazol-3(2H)-ones, which are potent and selective inhibitors of protein kinase R-like endoplasmic reticulum kinase (PERK). These inhibitors play a crucial role in the development of therapeutic agents for the treatment of various diseases, including cancer and neurodegenerative disorders, by modulating cellular stress responses and protein synthesis.
Additionally, the compound can be utilized in the synthesis of other bioactive molecules and drug candidates, owing to its unique structural features and reactivity. Its application in medicinal chemistry and drug discovery research is significant, as it enables the design and development of novel therapeutic agents with improved efficacy and selectivity.

Upstream product

• 91-63-4 2-methylquinoline 
• 73183-34-3 bis(pinacol)diborane 
• 877-42-9 6-Bromo-2-methyl-quinoline 

Downstream Products

• 1375062-48-8 C₁₆H₁₄N₂ 
• 1375062-50-2 C₂₅H₁₅F₆N₃O₂ 
• 1375062-49-9 C₂₅H₁₇F₆N₃O 

Relevant academic research and scientific papers

Iridium-Catalyzed Sequential Silylation and Borylation of Heteroarenes Based on Regioselective C?H Bond Activation

An iridium-catalyzed regioselective sequential silylation and borylation of heteroarenes was developed, which represents a rare example of unsymmetrical intermolecular C?H bond difunctionalization through the introduction of two different functionalities during a one-pot transformation. Although the substrate scope for the dehydrogenative silylation of heteroarenes has been limited mainly to electron-rich five-membered rings, the current reaction proceeds with both electron-rich and electron-deficient heteroarenes with the aid of heteroatom-directing C?H bond activation. The regioselectivity of the second borylation was controlled by both steric factors and the electronic effect of the silyl group installed in the first step. In combination with the classic cross-coupling reaction, this method provides rapid access to multisubstituted heteroarenes.

Heterocyclic compound with Wnt signal path inhibitory activity and application thereof

The invention provides a heterocyclic compound with Wnt signal path inhibitory activity. The heterocyclic compound and chemically acceptable salt, isotope, isomer and a crystal structure thereof are provided with a structure shown as the general formula I (see the formula in the description). The invention further provides application of the heterocyclic compound with the Wnt signal path inhibitory activity. The heterocyclic compound with the Wnt signal path inhibitory activity serves as effective antagonist of a Wnt signal path, and can be used for treating or preventing diseases caused by abnormity of the Wnt signal path.

ASYMMETRIC CATALYSTS

The present invention relates to asymmetric catalysts, including redox-reconfigurable asymmetric catalysts. Methods of producing compounds having one or more stereocenters using the asymmetric catalysts of the present invention are also disclosed.

Redox-configurable ambidextrous catalysis: Structural and mechanistic insight

A ligand capable of adopting two pseudo-enantiomeric helically chiral states when bound to copper has been applied as an asymmetric catalyst in the Michael addition of malonate substrates to nitrostyrenes. The absolute configuration of the helically chiral ligand is inverted upon oxidation/reduction of the copper center. In this way, the handedness of the Michael addition product (R/S) can be selected based on the handedness of the catalyst (Λ/Δ). Exciton coupled circular dichroism (ECCD) was used to identify which of the two pseudo-enantiomeric forms the catalyst adopted after reduction/oxidation, with additional support from X-ray crystallographic data. The synthesis of the ligand was achieved in five steps with an overall 61% yield. Enantiomeric excesses of the Michael addition products of up to 72% (S) and 70% (R) were obtained in acetonitrile. The ability to choose the handedness of the product based on the chiral state of the catalyst has been demonstrated with several different solvents, bases, nitrostyrene/malonate substrates, and prochiral malonate substrates. A combination of molecular modelling, crystal structure and kinetic data suggest that one urea moiety of the catalyst ligand likely binds the nitrostyrene substrate while blocking the Re face of the nitrostyrene in the transition state.

SUBSTITUTED QUINOLINES AND THEIR USE AS MEDICAMENTS

The invention relates to new substituted quinolines of formula (1) wherein R1 is a linear or branched C1-6-alkyl, wherein R1 may optionally be substituted by R3 which is selected from the group consisting of a three-, four-, five-, six- or seven-membered cycloalkl; a five-, six- or seven-membered, saturated heterocycle comprising one, two or three heteroatoms each independently selected from the group consisting of N, S and O; and a five- or six-membered heteroaryl comprising one, two or three heteroatoms each independently selected from the group consisting of N, S and O; wherein R3 may optionally be substituted further substituted as defined in claim 1 and wherein R2 is selected from the group consisting of halogen, phenyl, a five- or six-membered monocyclic heteroaryl comprising one, two or three heteroatoms each independently selected from the group consisting of N, S and O; a bicyclic, nine-, ten- or eleven-membered, either aromatic or non-aromatic, but not fully saturated heterocycle comprising one, two, three or four heteroatoms each independently selected from the group consisting of N, S and O; wherein R2 may optionally be further substituted as defined in claim 1, and their use in the preparation of medicaments for the treatment of disease such as asthma, COPD, allergic rhinitis, allergic dermatitis and rheumatoid arthritis.

Substituted Quinolines and Their Use As Medicaments

Disclosed are substituted quinolines of formula 1 wherein R1 and R2 are defined herein, the processing of making and using the same.