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118-10-5,MFCD00064372
Catalog No.:AA003281

118-10-5 | Cinchonine

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5g
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25g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003281
Chemical Name:
Cinchonine
CAS Number:
118-10-5
Molecular Formula:
C19H22N2O
Molecular Weight:
294.3908
MDL Number:
MFCD00064372
SMILES:
C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
NSC Number:
6176
Properties
Properties
 
BP:
464.5°C at 760 mmHg  
Form:
Solid  
MP:
256-266 °C  
Refractive Index:
223 ° (C=0.5, EtOH)  
Solubility:
0.25g/l  
Stability:
Light Sensitive  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
412  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
2.7  

Literature

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Crystal structure of quinine: the effects of vinyl and methoxy groups on molecular assemblies of Cinchona alkaloids cannot be ignored.

Journal: Chemistry, an Asian journal 20121101

Title: New insights into cinchonine-aluminium complexes and their application as chiral building blocks: unprecedented ligand-exchange processes in the presence of ZnR2 compounds.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20121015

Title: Homochiral crystallization of metal-organic silver frameworks: asymmetric [3+2] cycloaddition of an azomethine ylide.

Journal: Angewandte Chemie (International ed. in English) 20121001

Title: Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents.

Journal: Bioorganic & medicinal chemistry letters 20120901

Title: Evaluation of antibacterial and anti-biofilm activities of cinchona alkaloid derivatives against Staphylococcus aureus.

Journal: Natural product communications 20120901

Title: Development of a generic micellar electrokinetic chromatography method for the separation of 15 antimalarial drugs as a tool to detect medicine counterfeiting.

Journal: Electrophoresis 20120601

Title: Organocatalytic asymmetric conjugate addition of 3-monosubstituted oxindoles to (E)-1,4-diaryl-2-buten-1,4-diones: a strategy for the indirect enantioselective furanylation and pyrrolylation of 3-alkyloxindoles.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120521

Title: Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum.

Journal: Bioorganic & medicinal chemistry 20120515

Title: Medicinal plants used by various tribes of bangladesh for treatment of malaria.

Journal: Malaria research and treatment 20120101

Title: Secondary Metabolites from Plants Inhibiting ABC Transporters and Reversing Resistance of Cancer Cells and Microbes to Cytotoxic and Antimicrobial Agents.

Journal: Frontiers in microbiology 20120101

Title: Cinchonine Prevents High-Fat-Diet-Induced Obesity through Downregulation of Adipogenesis and Adipose Inflammation.

Journal: PPAR research 20120101

Title: Bioproduction of Cinchona alkaloids by the endophytic fungus Diaporthe sp. associated with Cinchona ledgeriana.

Journal: Chemical & pharmaceutical bulletin 20120101

Title: Silicon-based Lewis acid assisted cinchona alkaloid catalysis: highly enantioselective aza-Michael reaction under solvent-free conditions.

Journal: Organic letters 20111216

Title: The role of weak hydrogen bonds in chiral recognition.

Journal: Physical chemistry chemical physics : PCCP 20111028

Title: Desymmetrization of cyclohexadienones via asymmetric Michael reaction catalyzed by cinchonine-derived urea.

Journal: Organic letters 20111007

Title: Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases.

Journal: Acta crystallographica. Section C, Crystal structure communications 20110901

Title: Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells.

Journal: Environmental toxicology 20110801

Title: Novel molecularly imprinted microsphere using a single chiral monomer and chirality-matching (S)-ketoprofen template.

Journal: Journal of chromatography. A 20110617

Title: Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade.

Journal: Organic letters 20110506

Title: Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction.

Journal: Chirality 20110501

Title: A call for using natural compounds in the development of new antimalarial treatments - an introduction.

Journal: Malaria journal 20110101

Title: Natural products as starting points for future anti-malarial therapies: going back to our roots?

Journal: Malaria journal 20110101

Title: Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions.

Journal: Malaria journal 20110101

Title: Treatment of African children with severe malaria - towards evidence-informed clinical practice using GRADE.

Journal: Malaria journal 20110101

Title: Cinchona alkaloids are also produced by an endophytic filamentous fungus living in cinchona plant.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Rapid and green analytical method for the determination of quinoline alkaloids from Cinchona succirubra based on Microwave-Integrated Extraction and Leaching (MIEL) prior to high performance liquid chromatography.

Journal: International journal of molecular sciences 20110101

Title: Enantioselective radical addition to ketimines: a synthetic route towards α,α-disubstituted α-amino acids.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20101122

Title: Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay.

Journal: Antimicrobial agents and chemotherapy 20100901

Title: Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

Journal: Chirality 20100601

Title: Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization.

Journal: Talanta 20100315

Title: Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine.

Journal: Magnetic resonance in chemistry : MRC 20100101

Title: Empire and alternatives: Swietenia febrifuga and the Cinchona substitutes.

Journal: Medical history 20100101

Title: Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.

Journal: The journal of physical chemistry. B 20090827

Title: Metal complexes of cinchonine as chiral building blocks: a strategy for the construction of nanotubular architectures and helical coordination polymers.

Journal: Journal of the American Chemical Society 20090422

Title: Resolution of (+)-cinchonine and (-)-cinchonidine by phase-modulation fluorescence spectroscopy.

Journal: Analytica chimica acta 20090420

Title: Separation of Cinchona alkaloids on a novel strong cation-exchange-type chiral stationary phase-comparison with commercially available strong cation exchanger and reversed-phase packing materials.

Journal: Analytical and bioanalytical chemistry 20090201

Title: Highly enantioselective radical addition to N-benzoyl hydrazones using chiral ammonium salts.

Journal: Journal of the American Chemical Society 20081203

Title: Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.

Journal: Journal of the American Chemical Society 20081105

Title: Performance of electrospun nanofibers for SPE of drugs from aqueous solutions.

Journal: Journal of separation science 20081001

Title: Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.

Journal: Journal of the American Chemical Society 20081001

Title: A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.

Journal: The Journal of organic chemistry 20080905

Title: Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.

Journal: Accounts of chemical research 20080801

Title: An improved synthesis of 10,11-didehydro Cinchona alkaloids.

Journal: Chirality 20080301

Title: 1-[(Diethyl-amino-carbon-yl)meth-yl]-2-[hydr-oxy(6-methoxy-quinolin-4-yl)meth-yl]-5-vinyl-1-azoniabicyclo-[2.2.2]octane chloride monohydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20080201

Title: Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication.

Journal: Journal of fluorescence 20080101

Title: Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.

Journal: Chirality 20080101

Title: Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.

Journal: Journal of the American Chemical Society 20071226

Title: Increased uptake of quinine into the brain by inhibition of P-glycoprotein.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20071001

Title: Highly enantioselective direct aldol reaction catalyzed by cinchona derived primary amines.

Journal: Organic & biomolecular chemistry 20070921

Title: Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.

Journal: Organic & biomolecular chemistry 20070307

Title: Resolution and stereochemistry of tert-butylphenylphosphinous acid-borane.

Journal: The Journal of organic chemistry 20070202

Title: Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine.

Journal: Chirality 20070201

Title: Acceptability and efficacy of intra-rectal quinine alkaloids as a pre-transfer treatment of non-per os malaria in peripheral health care facilities in Mopti, Mali.

Journal: Malaria journal 20070101

Title: Asymmetric activation of tropos 2,2'-biphenol with cinchonine generates an effective catalyst for the asymmetric strecker reaction of N-tosyl-protected aldimines and ketoimines.

Journal: Angewandte Chemie (International ed. in English) 20070101

Title: Pilot feasibility study of an emergency paediatric kit for intra-rectal quinine administration used by the personnel of community-based health care units in Senegal.

Journal: Malaria journal 20070101

Title: Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.

Journal: Journal of the American Chemical Society 20061227

Title: Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.

Journal: The journal of physical chemistry. B 20061102

Title: Highly enantioselective cyanation of aldehydes catalyzed by a multicomponent titanium complex.

Journal: The Journal of organic chemistry 20060721

Title: Pharmacological strategies for overcoming multidrug resistance.

Journal: Current drug targets 20060701

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts.

Journal: Organic & biomolecular chemistry 20060407

Title: Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative.

Journal: Chemical communications (Cambridge, England) 20060321

Title: Stimulation of choline/Mg2+ antiport in rat erythrocytes by mefloquine.

Journal: Magnesium research 20060301

Title: Liquid chromatographic analysis of cinchona alkaloids in beverages.

Journal: Journal of AOAC International 20060101

Title: Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives.

Journal: Chemical communications (Cambridge, England) 20050921

Title: Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids.

Journal: Journal of the American Chemical Society 20050817

Title: Evaluation of magnesium fluxes in rat erythrocytes using a stable isotope of magnesium.

Journal: Frontiers in bioscience : a journal and virtual library 20050501

Title: Bioactive cinchona alkaloids from Remijia peruviana.

Journal: Journal of agricultural and food chemistry 20050323

Title: Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry.

Journal: Journal of the American Society for Mass Spectrometry 20050201

Title: Role of the solvent in the adsorption-desorption equilibrium of cinchona alkaloids between solution and a platinum surface: correlations among solvent polarity, cinchona solubility, and catalytic performance.

Journal: The journal of physical chemistry. B 20050113

Title: Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.

Journal: The Journal of organic chemistry 20041001

Title: Five new alkaloids from the leaves of Remijia peruviana.

Journal: Journal of natural products 20041001

Title: Defining determinant molecular properties for the blockade of the apamin-sensitive SKCa channel in guinea-pig hepatocytes: the influence of polarizability and molecular geometry.

Journal: Bioorganic & medicinal chemistry letters 20040802

Title: Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine.

Journal: Bioorganic chemistry 20040801

Title: Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040505

Title: Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040505

Title: Direct STM investigation of cinchona alkaloid adsorption on Cu(III).

Journal: Langmuir : the ACS journal of surfaces and colloids 20040413

Title: Conformational spaces of Cinchona alkaloids.

Journal: Chirality 20030801

Title: Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin.

Journal: Anti-cancer drugs 20030701

Title: Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone.

Journal: The Journal of organic chemistry 20030613

Title: Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.

Journal: Journal of the American Chemical Society 20030305

Title: The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20030217

Title: Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.

Journal: Bioorganic chemistry 20030201

Title: Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.

Journal: Chemical & pharmaceutical bulletin 20030101

Title: Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030101

Title: Hydrogenation of cinchona alkaloids over supported Pt catalyst.

Journal: Chirality 20030101

Title: The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.

Journal: Malaria journal 20030101

Title: Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials.

Journal: Journal of AOAC International 20030101

Title: In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.

Journal: Wiener klinische Wochenschrift 20030101

Title: Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination.

Journal: Organic letters 20020905

Title: [Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].

Journal: Se pu = Chinese journal of chromatography 20020901

Title: The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.

Journal: Journal of the American Chemical Society 20020814

Title: Unexpected change of the sense of the enantioselective hydrogenation of ethyl pyruvate catalyzed by a Pt-alumina-cinchona alkaloid system.

Journal: Chemical communications (Cambridge, England) 20020521

Title: Synthesis and evaluation of new antimalarial analogues of quinoline alkaloids derived from Cinchona ledgeriana Moens ex Trimen.

Journal: Bioorganic & medicinal chemistry letters 20020520

Title: Catalytic enantioselective fluorination of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.

Journal: Organic letters 20020221

Title: Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts.

Journal: The Journal of organic chemistry 20020111

Title: A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine.

Journal: The Analyst 20020101

Title: Cobalt complex of cinchonine: intermolecular interactions in two crystalline modifications.

Journal: Enantiomer 20020101

Title: New crystalline complex of quinine and quinidine.

Journal: Enantiomer 20020101

Title: Cinchoninium L-tartrate tetrahydrate.

Journal: Acta crystallographica. Section C, Crystal structure communications 20011201

Title: In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.

Journal: Planta medica 20011001

Title: Flexibility of CuCl4-tetrahedra in bis[cinchoninium tetrachlorocuprate(II)]trihydrate single crystals. X-ray diffraction and EPR studies.

Journal: Inorganic chemistry 20010827

Title: Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.

Journal: The Journal of pharmacy and pharmacology 20010701

Title: HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.

Journal: Planta medica 20010401

Title: Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane.

Journal: The Analyst 20010301

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Jin ZL, et al. Cinchonine activates endoplasmic reticulum stress-induced apoptosis in human liver cancer cells. Exp Ther Med. 2018 Jun;15(6):5046-5050.

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Tags:118-10-5 Molecular Formula|118-10-5 MDL|118-10-5 SMILES|118-10-5 Cinchonine |Heterocyclic_Building_Blocks