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(Unpublished)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Unpublished |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