33757-52-7

Upstream product

• 578-66-5 8-amino quinoline 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 2243-83-6 2-naphthaloyl chloride 
• 93-09-4 naphthalene-2-carboxylate 

Downstream Products

• 1647073-82-2 2,4-dinitro-N-(quinolin-8-yl)benzamide 
• 62-23-7 4-nitro-benzoic acid 
• 1395087-76-9 5-nitro-2-phenylbenzofuran-3-carbonitrile 

Relevant academic research and scientific papers

Polymorphs and salts of 4-nitro-N-(quinolin-8-yl)benzamide

Three polymorphs (I-III) of 4-nitro-N-(quinolin-8-yl)benzamide (L) arising from differences in their packing patterns are characterized. Out of the three polymorphs, two polymorphs (I and II) have extended chain of R22(10) type of hydrogen bonds involving

1, 8-naphthalic anhydride derivatives containing 8-(benzoylamino) quinoline as well as synthesis and application thereof

The invention discloses naphthalene anhydride derivatives containing 8-(benzoylamino) quinoline as well as a preparation method and application thereof, and belongs to the field of biological organicsynthesis. According to the naphthalic anhydride derivat

C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane

An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Catalyst- And oxidant-free electrochemical: para -selective hydroxylation of N -arylamides in batch and continuous-flow

Hydroxyl compounds serve as key building blocks in the preparation of biologically active natural products and drugs. Traditionally, hydroxylation of the aromatic ring is achieved using stoichiometric amounts of oxidants, which leads to low atom-economy, undesired by-products, potential explosion risk and environmental pollution. Recently, electrosynthesis has attracted increasing attention as it employs clean electrical energy to promote redox reactions avoiding the use of oxidants. However, due to the poor mass and heat transfers of batch cells, low productivity and selectivity limit its further application. Herein, we develop a catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at room temperature in batch and continuous-flow. This proposal features excellent position control and water, air and functional group tolerance. Also, it is easy to scale up with higher productivity and selectivity using a flow electrolysis cell.

Oxidative C-H/N-H Annulation of Aromatic Amides with Dialkyl Malonates: Access to Isoindolinones and Dihydrobenzoindoles

A copper-mediated oxidative C-H/N-H annulation of aromatic amides with dialkyl malonates has been presented to afford synthetically valuable dihydrobenzoindoles and isoindolinones. The reaction proceeds through direct oxidative C(sp2)-H/C(sp3)-H coupling followed by an intramolecular N-H/C(sp3)-H dehydrogenative coupling to deliver the target motifs with broad scope and functional group tolerance.

Copper-Mediated Aminoquinoline-Directed Radiofluorination of Aromatic C?H Bonds with K18F

A Cu-mediated ortho-C?H radiofluorination of aromatic carboxylic acids that are protected as 8-aminoquinoline benzamides is described. The method uses K18F and is compatible with a wide range of functional groups. The reaction is showcased in t

Electrooxidative amination of sp2 C-H bonds: Coupling of amines with aryl amides via copper catalysis

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis. However, the use of C-H activation for sp2 C-N bond formation remains one of the major challenges in the field of cross-coupling chemistry. Described herein is the first example of the synergistic combination of copper catalysis and electrocatalysis for aryl C-H amination under mild reaction conditions in an atom-and step-economical manner with the liberation of H2 as the sole and benign byproduct.

Synthesis and mechanistic studies of quinolin-chlorobenzothioate derivatives with proteasome inhibitory activity in pancreatic cancer cell lines

Inhibition of proteasome activity blocks the degradation of dysfunctional proteins and induces cancer cell death due to cellular stress. Thus, proteasome inhibitors represent an attractive class of anticancer agents, and bortezomib, carfilzomib and ixazomib have been FDA-approved to treat multiple myeloma. However, cancer cells acquire resistance to these inhibitors through point mutations in the proteasome catalytic subunit or induction of alternative compensatory mechanisms. In this study, we identified a quinolin-chlorobenzothioate, QCBT7, as a new proteasome inhibitor showing cytotoxicity in a panel of cancer cell lines. QCBT7 is a more stable derivative of quinoline-8-thiol that targets the regulatory subunit instead of the catalytic subunit of the proteasome. QCBT7 caused the accumulation of ubiquitylated proteins in the cancer cells, indicating its proteasome inhibitory activity. Additionally, QCBT7 increased the expression of a set of genes (PFKFB4, CHOP, HMOX1 and SLC7A11) at both nascent RNA and protein levels, similarly to the known proteasome inhibitors MG132 and ixazomib. Together, QCBT7 induces proteasome inhibition, hypoxic response, endoplasmic reticulum stress and glycolysis, finally leading to cell death. Importantly, we have identified PFKFB4 as a potential biomarker of proteasome inhibitors that can be used to monitor treatment response.

TANKYRASE INHIBITORS

The invention relates to compounds of formula (I): (I) and salts, solvates, tautomers and stereoisomers thereof, where the definitions of the variables are provided herein. The invention also relates to pharmaceutical compositions comprising compounds of formula (I) as well as for the use of such compounds as tankyrase inhibitors and for the treatment of diseases such as cancer.