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Synthesis of Pentafluorosulfanyl Analogs of Mefloquine

Mo, Tingting (2010) Synthesis of Pentafluorosulfanyl Analogs of Mefloquine. Master's Thesis, University of Pittsburgh. (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
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:, etd-05032010-114523
Date Deposited: 10 Nov 2011 19:43
Last Modified: 15 Nov 2016 13:43


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