Mo, Tingting
(2010)
Synthesis of Pentafluorosulfanyl Analogs of Mefloquine.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
The pentafluorosulfanyl (SF5) group is of increasing interest as a functional group in pharmaceutical and agrochemical research, and was recently labeled as the "substituent of the future". It imparts unique properties to organic compounds and enhances their biological activities because of its high electronegativity, substantial steric effect, significant hydrophobicity and high chemical resistance. To improve the activity and alleviate the neurotoxicity of the anti-malarial drug Mefloquine, we introduced the SF5 group into the quinoline methanolamine scaffold in place of the trifluoromethyl (CF3) group. Three novel mefloquine analogs were synthesized in high yields from simple phenyl SF5 building blocks through short synthetic routes. Two analogs were found to have improved activity and selectivity against malarial parasites, and one analog demonstrated lower membrane permeability, which is potentially advantageous for the reduction of the neurotoxic side effects. As part of this work, we also report the first SF5-containing quinoline heterocycles and the first ortho SF5 aniline.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
20 September 2010 |
| Date Type: |
Completion |
| Defense Date: |
13 May 2010 |
| Approval Date: |
20 September 2010 |
| Submission Date: |
3 May 2010 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| 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: |
mefloquine; pentafluorosulfanyl; synthesis |
| Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-05032010-114523/, etd-05032010-114523 |
| Date Deposited: |
10 Nov 2011 19:43 |
| Last Modified: |
15 Nov 2016 13:43 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/7773 |
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