200,000+ products from a single source!

sales@angenechem.com

Home > Quinoline > 118-10-5

118-10-5

118-10-5 | (S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol

CAS No: 118-10-5 Catalog No: AG0032AT MDL No:MFCD00064372

Product Description

Catalog Number:
AG0032AT
Chemical Name:
(S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol
CAS Number:
118-10-5
Molecular Formula:
C19H22N2O
Molecular Weight:
294.3908
MDL Number:
MFCD00064372
IUPAC Name:
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
InChI:
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChI Key:
KMPWYEUPVWOPIM-QAMTZSDWSA-N
SMILES:
C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O
EC Number:
204-234-6
UNII:
V43X79NZCD
NSC Number:
6176

Properties

Complexity:
412  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
294.173g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
294.398g/mol
Monoisotopic Mass:
294.173g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
36.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7  

Literature

Title Journal
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Crystal structure of quinine: the effects of vinyl and methoxy groups on molecular assemblies of Cinchona alkaloids cannot be ignored. Chemistry, an Asian journal 20121101
New insights into cinchonine-aluminium complexes and their application as chiral building blocks: unprecedented ligand-exchange processes in the presence of ZnR2 compounds. Chemistry (Weinheim an der Bergstrasse, Germany) 20121015
Homochiral crystallization of metal-organic silver frameworks: asymmetric [3+2] cycloaddition of an azomethine ylide. Angewandte Chemie (International ed. in English) 20121001
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. Bioorganic & medicinal chemistry letters 20120901
Evaluation of antibacterial and anti-biofilm activities of cinchona alkaloid derivatives against Staphylococcus aureus. Natural product communications 20120901
Development of a generic micellar electrokinetic chromatography method for the separation of 15 antimalarial drugs as a tool to detect medicine counterfeiting. Electrophoresis 20120601
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. Chemistry (Weinheim an der Bergstrasse, Germany) 20120521
Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum. Bioorganic & medicinal chemistry 20120515
Medicinal plants used by various tribes of bangladesh for treatment of malaria. Malaria research and treatment 20120101
Secondary Metabolites from Plants Inhibiting ABC Transporters and Reversing Resistance of Cancer Cells and Microbes to Cytotoxic and Antimicrobial Agents. Frontiers in microbiology 20120101
Cinchonine Prevents High-Fat-Diet-Induced Obesity through Downregulation of Adipogenesis and Adipose Inflammation. PPAR research 20120101
Bioproduction of Cinchona alkaloids by the endophytic fungus Diaporthe sp. associated with Cinchona ledgeriana. Chemical & pharmaceutical bulletin 20120101
Silicon-based Lewis acid assisted cinchona alkaloid catalysis: highly enantioselective aza-Michael reaction under solvent-free conditions. Organic letters 20111216
The role of weak hydrogen bonds in chiral recognition. Physical chemistry chemical physics : PCCP 20111028
Desymmetrization of cyclohexadienones via asymmetric Michael reaction catalyzed by cinchonine-derived urea. Organic letters 20111007
Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases. Acta crystallographica. Section C, Crystal structure communications 20110901
Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells. Environmental toxicology 20110801
Novel molecularly imprinted microsphere using a single chiral monomer and chirality-matching (S)-ketoprofen template. Journal of chromatography. A 20110617
Facile synthesis of enantioenriched Cγ-tetrasubstituted α-amino acid derivatives via an asymmetric nucleophilic addition/protonation cascade. Organic letters 20110506
Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction. Chirality 20110501
A call for using natural compounds in the development of new antimalarial treatments - an introduction. Malaria journal 20110101
Natural products as starting points for future anti-malarial therapies: going back to our roots? Malaria journal 20110101
Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal 20110101
Treatment of African children with severe malaria - towards evidence-informed clinical practice using GRADE. Malaria journal 20110101
Cinchona alkaloids are also produced by an endophytic filamentous fungus living in cinchona plant. Chemical & pharmaceutical bulletin 20110101
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. International journal of molecular sciences 20110101
Enantioselective radical addition to ketimines: a synthetic route towards α,α-disubstituted α-amino acids. Chemistry (Weinheim an der Bergstrasse, Germany) 20101122
Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay. Antimicrobial agents and chemotherapy 20100901
Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate. Chirality 20100601
Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. Talanta 20100315
Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine. Magnetic resonance in chemistry : MRC 20100101
Empire and alternatives: Swietenia febrifuga and the Cinchona substitutes. Medical history 20100101
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids. The journal of physical chemistry. B 20090827
Metal complexes of cinchonine as chiral building blocks: a strategy for the construction of nanotubular architectures and helical coordination polymers. Journal of the American Chemical Society 20090422
Resolution of (+)-cinchonine and (-)-cinchonidine by phase-modulation fluorescence spectroscopy. Analytica chimica acta 20090420
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. Analytical and bioanalytical chemistry 20090201
Highly enantioselective radical addition to N-benzoyl hydrazones using chiral ammonium salts. Journal of the American Chemical Society 20081203
Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. Journal of the American Chemical Society 20081105
Performance of electrospun nanofibers for SPE of drugs from aqueous solutions. Journal of separation science 20081001
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis. Journal of the American Chemical Society 20081001
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers. The Journal of organic chemistry 20080905
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. Accounts of chemical research 20080801
An improved synthesis of 10,11-didehydro Cinchona alkaloids. Chirality 20080301
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. Acta crystallographica. Section E, Structure reports online 20080201
Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication. Journal of fluorescence 20080101
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids. Chirality 20080101
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces. Journal of the American Chemical Society 20071226
Increased uptake of quinine into the brain by inhibition of P-glycoprotein. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20071001
Highly enantioselective direct aldol reaction catalyzed by cinchona derived primary amines. Organic & biomolecular chemistry 20070921
Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones. Organic & biomolecular chemistry 20070307
Resolution and stereochemistry of tert-butylphenylphosphinous acid-borane. The Journal of organic chemistry 20070202
Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. Chirality 20070201
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. Malaria journal 20070101
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. Angewandte Chemie (International ed. in English) 20070101
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. Malaria journal 20070101
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces. Journal of the American Chemical Society 20061227
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals. The journal of physical chemistry. B 20061102
Highly enantioselective cyanation of aldehydes catalyzed by a multicomponent titanium complex. The Journal of organic chemistry 20060721
Pharmacological strategies for overcoming multidrug resistance. Current drug targets 20060701
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts. Organic & biomolecular chemistry 20060407
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. Chemical communications (Cambridge, England) 20060321
Stimulation of choline/Mg2+ antiport in rat erythrocytes by mefloquine. Magnesium research 20060301
Liquid chromatographic analysis of cinchona alkaloids in beverages. Journal of AOAC International 20060101
Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives. Chemical communications (Cambridge, England) 20050921
Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. Journal of the American Chemical Society 20050817
Evaluation of magnesium fluxes in rat erythrocytes using a stable isotope of magnesium. Frontiers in bioscience : a journal and virtual library 20050501
Bioactive cinchona alkaloids from Remijia peruviana. Journal of agricultural and food chemistry 20050323
Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry. Journal of the American Society for Mass Spectrometry 20050201
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. The journal of physical chemistry. B 20050113
Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. The Journal of organic chemistry 20041001
Five new alkaloids from the leaves of Remijia peruviana. Journal of natural products 20041001
Defining determinant molecular properties for the blockade of the apamin-sensitive SKCa channel in guinea-pig hepatocytes: the influence of polarizability and molecular geometry. Bioorganic & medicinal chemistry letters 20040802
Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine. Bioorganic chemistry 20040801
Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040505
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040505
Direct STM investigation of cinchona alkaloid adsorption on Cu(III). Langmuir : the ACS journal of surfaces and colloids 20040413
Conformational spaces of Cinchona alkaloids. Chirality 20030801
Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin. Anti-cancer drugs 20030701
Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone. The Journal of organic chemistry 20030613
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives. Journal of the American Chemical Society 20030305
The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach. Chemphyschem : a European journal of chemical physics and physical chemistry 20030217
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s. Bioorganic chemistry 20030201
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens. Chemical & pharmaceutical bulletin 20030101
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030101
Hydrogenation of cinchona alkaloids over supported Pt catalyst. Chirality 20030101
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malaria journal 20030101
Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials. Journal of AOAC International 20030101
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand. Wiener klinische Wochenschrift 20030101
Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination. Organic letters 20020905
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers]. Se pu = Chinese journal of chromatography 20020901
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes. Journal of the American Chemical Society 20020814
Unexpected change of the sense of the enantioselective hydrogenation of ethyl pyruvate catalyzed by a Pt-alumina-cinchona alkaloid system. Chemical communications (Cambridge, England) 20020521
Synthesis and evaluation of new antimalarial analogues of quinoline alkaloids derived from Cinchona ledgeriana Moens ex Trimen. Bioorganic & medicinal chemistry letters 20020520
Catalytic enantioselective fluorination of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. Organic letters 20020221
Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts. The Journal of organic chemistry 20020111
A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine. The Analyst 20020101
Cobalt complex of cinchonine: intermolecular interactions in two crystalline modifications. Enantiomer 20020101
New crystalline complex of quinine and quinidine. Enantiomer 20020101
Cinchoninium L-tartrate tetrahydrate. Acta crystallographica. Section C, Crystal structure communications 20011201
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense. Planta medica 20011001
Flexibility of CuCl4-tetrahedra in bis[cinchoninium tetrachlorocuprate(II)]trihydrate single crystals. X-ray diffraction and EPR studies. Inorganic chemistry 20010827
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. The Journal of pharmacy and pharmacology 20010701
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations. Planta medica 20010401
Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane. The Analyst 20010301
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products 19910101

© 2019 Angene International Limited. All rights Reserved.