Optical isomers of aryl-2-piperidylmethanol antimalarial agents. Preparation, optical purity, and absolute stereochemistry

PMID: 4588275Feb 1, 1974Paper

Optical isomers of aryl-2-piperidylmethanol antimalarial agents. Preparation, optical purity, and absolute stereochemistry

Journal of Medicinal Chemistry

F I Carroll, J T Blackwell

Abstract

No abstract listed.

Citations

Fifteen years of research of bioactive alkaloids.

Jan 1, 1992·Medicinal Research Reviews·A Brossi

Two-step liquid-phase microextraction and high-performance liquid chromatography for the simultaneous analysis of the enantiomers of mefloquine and its main metabolite carboxymefloquine in plasma

Feb 3, 2009·Analytical and Bioanalytical Chemistry·Igor Rafael dos Santos Magalhães, Pierina Sueli Bonato

Antimalarial activity of optical isomers of quinacrine dihydrochloride against chloroquine-sensitive and -resistant Plasmodium falciparum in vitro

Dec 11, 1991·Biochemical Pharmacology·R V WebsterD C Warhurst

Absence of antimalarial activity or interaction with mefloquine enantiomers in vitro of the main human metabolite of mefloquine

Mar 1, 1991·Transactions of the Royal Society of Tropical Medicine and Hygiene·L K BascoJ Le Bras

Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues

Nov 8, 2002·Il Farmaco·Patricia C LimaCarlos A M Fraga

Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents

Aug 27, 1998·Pharmacology & Therapeutics·M Foley, L Tilley

Determining the absolute configuration of (+)-mefloquine HCl, the side-effect-reducing enantiomer of the antimalaria drug Lariam

Dec 14, 2011·Journal of the American Chemical Society·Manuel SchmidtUwe M Reinscheid

Asymmetric total synthesis of the antimalarial drug (+)-mefloquine hydrochloride via chiral N-amino cyclic carbamate hydrazones

May 28, 2011·Organic Letters·John D KnightDon M Coltart

In vitro activity of the enantiomers of mefloquine, halofantrine and enpiroline against Plasmodium falciparum

May 1, 1992·British Journal of Clinical Pharmacology·L K BascoJ Le Bras

Stereoselective passage of mefloquine through the blood-brain barrier in the rat

Dec 24, 1997·The Journal of Pharmacy and Pharmacology·S BaudryR Farinotti

Identification of (+)-erythro-mefloquine as an active enantiomer with greater efficacy than mefloquine against Mycobacterium avium infection in mice.

May 23, 2012·Antimicrobial Agents and Chemotherapy·Luiz E BermudezLowell S Young

Antimalarial activities of various 4-quinolonemethanols with special attention to WR-142,490 (mefloquine).

Jun 1, 1978·Antimicrobial Agents and Chemotherapy·L H SchmidtD Vaughan

Crystal structure and molecular structure of mefloquine methylsulfonate monohydrate: implications for a malaria receptor.

Nov 1, 1991·Antimicrobial Agents and Chemotherapy·J M Karle, I L Karle

A small-fish model for behavioral-toxicological screening of new antimalarial drugs: a comparison between erythro- and threo-mefloquine

Apr 18, 2015·BMC Research Notes·Hans MaaswinkelWei Weng

Mefloquine and psychotomimetics share neurotransmitter receptor and transporter interactions in vitro

Feb 4, 2014·Psychopharmacology·Aaron JanowskyMichael K Riscoe

Mefloquine and Its Enantiomers Are Active against Mycobacterium tuberculosis In Vitro and in Macrophages

Jan 13, 2015·Tuberculosis Research and Treatment·Luiz E Bermudez, Laura Meek

Enhancement of solubility of drug salts by hydrophilic counterions: properties of organic salts of an antimalarial drug

May 1, 1976·Journal of Pharmaceutical Sciences·S AgharkarT Higuchi

In vitro effects of racemates, separate enantiomers and major metabolites of mefloquine and halofantrine on metoprolol biotransformation by rat liver microsomes

Jul 30, 1999·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·B BauneR Farinotti

Schistosoma mansoni: antischistosomal activity of the four optical isomers and the two racemates of mefloquine on schistosomula and adult worms in vitro and in vivo

Aug 25, 2010·Experimental Parasitology·Theresia ManneckJennifer Keiser

Novel chiral selector based on mefloquine--a comparative NMR study to elucidate intermolecular interactions with acidic chiral selectands

Apr 18, 2012·Chirality·Michal KohoutWolfgang Lindner

Asymmetric Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride

Sep 23, 2016·The Journal of Organic Chemistry·Ettore J Rastelli, Don M Coltart

A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles

Dec 15, 2015·Angewandte Chemie·Imants KreitussJeffrey W Bode

Comparative enantioseparations with native beta-cyclodextrin and heptakis-(2-O-methyl- 3,6-di-O-sulfo)-beta-cyclodextrin in capillary electrophoresis

Sep 11, 2002·Electrophoresis·Bezhan ChankvetadzeGottfried Blaschke

Attrition-Enhanced Deracemization of the Antimalaria Drug Mefloquine

Dec 7, 2018·Angewandte Chemie·Anthonius H J EngwerdaElias Vlieg

The present status of malaria chemotherapy: mefloquine, a novel antimalarial

Jan 1, 1981·Medicinal Research Reviews·T R Sweeney

Trapped in misbelief for almost 40 years: selective synthesis of the four stereoisomers of mefloquine

Nov 15, 2013·Chemistry : a European Journal·Nina SchützenmeisterAndrei Leonov

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

Jan 17, 2013·Organic & Biomolecular Chemistry·Russell J JohnsonMatthew A J Duncton

The absolute configuration of (+)- and (-)-erythro-mefloquine

Apr 26, 2013·Angewandte Chemie·Michael MüllerChristian Griesinger

Concise synthesis and antimalarial activity of all four mefloquine stereoisomers using a highly enantioselective catalytic borylative alkene isomerization

Jul 3, 2013·Angewandte Chemie·Jinyue Ding, Dennis G Hall

A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines

Oct 1, 2015·Angewandte Chemie·Ettore J Rastelli, Don M Coltart

Absolute Configuration and Antimalarial Activity of erythro-Mefloquine Enantiomers

Jul 1, 2013·ChemPlusChem·Alexandra Dassonville-KlimptPascal Sonnet

Crystal structures and other properties of ephedrone (methcathinone) hydrochloride, N -acetylephedrine and N -acetylephedrone

Jan 15, 2019·Forensic Toxicology·Piotr KuśAleksander Sochanik

The chemotherapy of rodent malaria. LII. Response of Plasmodium yoelii ssp. NS to mefloquine and its enantiomers

Oct 1, 1995·Annals of Tropical Medicine and Parasitology·W PetersD Stürchler

Crystal structure of (-)-mefloquine hydrochloride reveals consistency of configuration with biological activity.

Apr 18, 2002·Antimicrobial Agents and Chemotherapy·Jean M Karle, Isabella L Karle

Chiral Vicinal Diamines Derived from Mefloquine.

Jul 28, 2021·The Journal of Organic Chemistry·Dawid J KucharskiPrzemysław J Boratyński

General Quantum-Based NMR Method for the Assignment of Absolute Configuration by Single or Double Derivatization: Scope and Limitations

Sep 6, 2018·The Journal of Organic Chemistry·María M ZanardiAriel M Sarotti

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Antimalarial Agents (ASM)

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Antimalarial Agents

Antimalarial agents, also known as antimalarials, are designed to prevent or cure malaria. Discover the latest research on antimalarial agents here.

Optical isomers of aryl-2-piperidylmethanol antimalarial agents. Preparation, optical purity, and absolute stereochemistry

Abstract

Citations

Fifteen years of research of bioactive alkaloids.

Two-step liquid-phase microextraction and high-performance liquid chromatography for the simultaneous analysis of the enantiomers of mefloquine and its main metabolite carboxymefloquine in plasma

Antimalarial activity of optical isomers of quinacrine dihydrochloride against chloroquine-sensitive and -resistant Plasmodium falciparum in vitro

Absence of antimalarial activity or interaction with mefloquine enantiomers in vitro of the main human metabolite of mefloquine

Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues

Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents

Determining the absolute configuration of (+)-mefloquine HCl, the side-effect-reducing enantiomer of the antimalaria drug Lariam

Asymmetric total synthesis of the antimalarial drug (+)-mefloquine hydrochloride via chiral N-amino cyclic carbamate hydrazones

In vitro activity of the enantiomers of mefloquine, halofantrine and enpiroline against Plasmodium falciparum

Stereoselective passage of mefloquine through the blood-brain barrier in the rat

Identification of (+)-erythro-mefloquine as an active enantiomer with greater efficacy than mefloquine against Mycobacterium avium infection in mice.

Antimalarial activities of various 4-quinolonemethanols with special attention to WR-142,490 (mefloquine).

Crystal structure and molecular structure of mefloquine methylsulfonate monohydrate: implications for a malaria receptor.

A small-fish model for behavioral-toxicological screening of new antimalarial drugs: a comparison between erythro- and threo-mefloquine

Mefloquine and psychotomimetics share neurotransmitter receptor and transporter interactions in vitro

Mefloquine and Its Enantiomers Are Active against Mycobacterium tuberculosis In Vitro and in Macrophages

Enhancement of solubility of drug salts by hydrophilic counterions: properties of organic salts of an antimalarial drug

In vitro effects of racemates, separate enantiomers and major metabolites of mefloquine and halofantrine on metoprolol biotransformation by rat liver microsomes

Schistosoma mansoni: antischistosomal activity of the four optical isomers and the two racemates of mefloquine on schistosomula and adult worms in vitro and in vivo

Novel chiral selector based on mefloquine--a comparative NMR study to elucidate intermolecular interactions with acidic chiral selectands

Asymmetric Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride

A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles

Comparative enantioseparations with native beta-cyclodextrin and heptakis-(2-O-methyl- 3,6-di-O-sulfo)-beta-cyclodextrin in capillary electrophoresis

Attrition-Enhanced Deracemization of the Antimalaria Drug Mefloquine

The present status of malaria chemotherapy: mefloquine, a novel antimalarial

Trapped in misbelief for almost 40 years: selective synthesis of the four stereoisomers of mefloquine

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

The absolute configuration of (+)- and (-)-erythro-mefloquine

Concise synthesis and antimalarial activity of all four mefloquine stereoisomers using a highly enantioselective catalytic borylative alkene isomerization

A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines

Absolute Configuration and Antimalarial Activity of erythro-Mefloquine Enantiomers

Crystal structures and other properties of ephedrone (methcathinone) hydrochloride, N -acetylephedrine and N -acetylephedrone

The chemotherapy of rodent malaria. LII. Response of Plasmodium yoelii ssp. NS to mefloquine and its enantiomers

Crystal structure of (-)-mefloquine hydrochloride reveals consistency of configuration with biological activity.

Chiral Vicinal Diamines Derived from Mefloquine.

General Quantum-Based NMR Method for the Assignment of Absolute Configuration by Single or Double Derivatization: Scope and Limitations

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