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Usage

Uses

Used in Pharmaceutical Industry:
QUININONE (50 MG) is used as an antimalarial agent for its ability to combat malaria in mice. Its effectiveness in treating this disease makes it a valuable asset in the fight against malaria, a significant global health concern.
Used in Medical Research:
QUININONE (50 MG) is used as a research tool for studying the binding of drug-induced antibodies to human platelets. This application aids in understanding the interactions between drugs, antibodies, and platelets, which can be crucial for developing new therapeutic strategies and improving patient care.

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 9-epiquinine 
• 64-19-7 acetic acid 
• 56-54-2 quinidine 
• 130-95-0 Quinine 
• 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 
• 56-54-2 quinindine 
• 130-95-0 quinine 

Downstream Products

• 86-68-0 6-methoxyquinoline-4-carboxylic acid 
• 345223-64-5 isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate 
• 130-95-0 quinine 
• 56-54-2 quinine 
• 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 
• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 
• 147780-50-5 (+)-R-mequitazine 
• 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 
• 345223-69-0 7-(2-benzyloxy-ethyl)-3,4,4a,5,6,8a-hexahydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

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.

Early and Late Steps of Quinine Biosynthesis

The enzymatic basis for quinine 1 biosynthesis was investigated. Transcriptomic data from the producing plant led to the discovery of three enzymes involved in the early and late steps of the pathway. A medium-chain alcohol dehydrogenase (CpDCS) and an esterase (CpDCE) yielded the biosynthetic intermediate dihydrocorynantheal 2 from strictosidine aglycone 3. Additionally, the discovery of an O-methyltransferase specific for 6′-hydroxycinchoninone 4 suggested the final step order to be cinchoninone 16/17 hydroxylation, methylation, and keto-reduction.

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.

VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE

The present invention relates to the use of the vinyl quinuclidine enantiomer (R) of the following formula 2 as a synthesis intermediate in the preparation of (R)-mequitazine.

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

Asymmetric synthesis of (+)-mequitazine from quinine

The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.

Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine

(Chemical Presented) Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aromatic and aliphatic aldehydes gave epoxides with perfect enantioselectivities and the highest diastereoselectivities reported to date. In addition reactions with imines gave aziridines again with the highest enantioselectivities and diastereoselectivities reported to date. The reactions are scaleable, and the sulfide can be reisolated in high yield. The epoxidation has been used as the key step in a convergent and stereoselective synthesis of each of the diastereoisomers of the cinchona alkaloids, quinine and quinidine. Copyright

Rabe rest in peace: Confirmation of the rabe-kindler conversion of d-quinotoxine into quinine: Experimental affirmation of the woodward-doering formal total synthesis of quinine

(Chemical Equation Presented) Put to rest: The three-step conversion of d-quinotoxine into quinine, as originally reported by Rabe and Kindler in 1918, has been experimentally verified. This conversion serves to reaffirm the formal total synthesis of quin

A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

The AB ring system found in the manzamine A and related alkaloids has been prepared from (-)-quinine by a short enantioselective route. The key step in the sequence is a ruthenium-catalysed ring-closing enyne metathesis re action which delivers a bicyclic diene in good yield. The functionality required for further elaboration of the AB system has been installed by sequential regioselective hydroboration and stereoselective catalytic aminohydroxylation.