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Enantioselective Synthesis of Mefloquine Analogs and Their Derivatives

Nakamura, Akira (2010) Enantioselective Synthesis of Mefloquine Analogs and Their Derivatives. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Mefloquine is a clinically useful anti-malarial compound active against strains of the Plasmodium parasite. The behavioral effects of each of the enantiomers of mefloquine were assessed. The (+)-(11R,12S)-enantiomer showed higher activity against Plasmodium falciparum. Progress has been made toward the enantioselective synthesis of the (+)-(11R,12S)-8-chloromefloquine analog. An enantiometically pure product was obtained by using hydrozirconation followed by a zinc-palladium catalyzed Negishi cross-coupling reaction and a Sharpless dihydroxylation as key steps.A series of mefloquine analogs have been developed to facilitate future structure-activity relationships and the development of new antimalaria agents. A recent study suggested an increase in the potency with electron-withdrawing groups at both the 2- and 8-positions of the quinoline ring. According to this concept, six new 8-position derivatives were synthesized via a palladium mediated coupling reaction.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Nakamura, Akiraakn8@pitt.edu, Nachemura.org@gmail.comAKN8
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberChapman, Tobytchapman@imap.pitt.eduTCHAPMAN
Date: 26 January 2010
Date Type: Completion
Defense Date: 30 October 2009
Approval Date: 26 January 2010
Submission Date: 30 November 2009
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Mefloqune; Palladium cross-coupling
Other ID: http://etd.library.pitt.edu/ETD/available/etd-11302009-133233/, etd-11302009-133233
Date Deposited: 10 Nov 2011 20:07
Last Modified: 15 Nov 2016 13:52
URI: http://d-scholarship.pitt.edu/id/eprint/9885

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