84-31-1

Basic information

• Product Name: QUININONE (50 MG)
• Synonyms: QUININONE (50 MG);(8alpha)-6'-methoxycinchonan-9-one;(8α)-6'-Methoxycinchonan-9-one;(5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanone;(6-methoxy-4-quinolyl)-(5-vinylquinuclidin-2-yl)methanone;Quininone (Quinine Sulfate IMpurity);Quininoe
• CAS NO: 84-31-1
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.40088
• EINECS: 201-524-4
• Mol File: 84-31-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 108° (rapid heating)
• Boiling Point: 461.02°C (rough estimate)
• Flash Point: 242.8°C
• Appearance: /
• Density: 1.1478 (rough estimate)
• Vapor Pressure: 2.72E-09mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Water Solubility: 3mg/L(20 oC)
• CAS DataBase Reference: QUININONE (50 MG)(CAS DataBase Reference)
• NIST Chemistry Reference: QUININONE (50 MG)(84-31-1)
• EPA Substance Registry System: QUININONE (50 MG)(84-31-1)

Safety Data

• Hazardous Substances Data: 84-31-1(Hazardous Substances Data)

Usage

Uses

Quininone has been shown to have antimalarial activity in mice. Quininone has been shown to aid the binding of drug-induced antibodies to human platelets.

InChI:InChI=1/C20H22N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19H,1,7,9-10,12H2,2H3

Upstream product

• 56-54-2 quinidine 
• 56-54-2 (6-Methoxy-quinolin-4-yl)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol 
• 908578-83-6 N-bromoquinotoxine 
• 130-95-0 quinine 
• 56-54-2 quinindine 
• 130-95-0 Quinine 
• 64-19-7 acetic acid 
• 56-54-2 9-epiquinine 

Downstream Products

• 130-95-0 quinine 
• 56-54-2 quinine 
• 86-68-0 6-methoxyquinoline-4-carboxylic acid 
• 345223-64-5 isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate 
• 1393601-64-3 (8R,9S)-6'-methoxy-9-phenyl-9-cinchonanol 
• 1393601-69-8 (8S,9R)-6'-methoxy-9-phenyl-9-cinchonanol 
• 1393601-66-5 (8R,9S)-6'-methoxy-9-(3-aminophenyl)-9-cinchonanol 
• 52346-11-9 tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate 
• 52390-26-8 4a(S),8a(R)-2-benzoyloctahydro-6(2H)-isoquinolinone 
• 52346-14-2 4a(S),8a(R)-2-benzoyl-1,3,4,4a,5,8a-hexahydro-6(2H)-isoquinolinone 
• 52346-13-1 N-benzoylmeroquinene tert-butyl ester 
• 147780-50-5 (+)-R-mequitazine 
• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 
• 345223-69-0 7-(2-benzyloxy-ethyl)-3,4,4a,5,6,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Image-Based Morphological Profiling Identifies a Lysosomotropic, Iron-Sequestering Autophagy Inhibitor

Chemical proteomics is widely applied in small-molecule target identification. However, in general it does not identify non-protein small-molecule targets, and thus, alternative methods for target identification are in high demand. We report the discovery of the autophagy inhibitor autoquin and the identification of its molecular mode of action using image-based morphological profiling in the cell painting assay. A compound-induced fingerprint representing changes in 579 cellular parameters revealed that autoquin accumulates in lysosomes and inhibits their fusion with autophagosomes. In addition, autoquin sequesters Fe2+ in lysosomes, resulting in an increase of lysosomal reactive oxygen species and ultimately cell death. Such a mechanism of action would have been challenging to unravel by current methods. This work demonstrates the potential of the cell painting assay to deconvolute modes of action of small molecules, warranting wider application in chemical biology.

Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids

Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds (a and 2a) and six series of quinoline derivatives (3a-f) for their antifungal activities. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. Significantly, compounds 3f-4 (EC50 = 0.41 μg/mL) and 3f-28 (EC50 = 0.55 μg/mL) displayed the superior in vitro fungicidal activity and the potent in vivo curative effect against Sclerotinia sclerotiorum. Preliminary mechanism studies showed that compounds 3f-4 and 3f-28 could cause changes in the cell membrane permeability, accumulation of reactive oxygen species, loss of mitochondrial membrane potential, and effective inhibition of germination and formation of S. sclerotiorum sclerotia. These results indicate that compounds 3f-4 and 3f-28 are novel potential fungicidal candidates against S. sclerotiorum derived from natural products.

Synthetic approaches to 9-arylated Cinchona alkaloids: Stereoselective addition of Grignard reagents to cinchonanones and hydroxylation of 9-phenylcinchonanes

All 8,9-isomers of the 9-phenyl Cinchona alkaloids were obtained by autoxidation of 9-deoxy-9-phenyl-alkaloids and by the addition of Grignard reagents to the respective ketones. The diastereoselective addition of phenyl-, methyl-, and vinylmagnesium reag