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Synthesis of Retigabine Analogues for the Treatment of Tinnitus and Progress Towards a Concise Route to XJB-5-131

Reed, Nicholas (2015) Synthesis of Retigabine Analogues for the Treatment of Tinnitus and Progress Towards a Concise Route to XJB-5-131. Master's Thesis, University of Pittsburgh. (Unpublished)

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The first part of this thesis describes the synthesis of retigabine analogues for the treatment of tinnitus. Retigabine is a clinically proven anticonvulsant that modulates potassium ion channel activity and has been shown to stop the onset of tinnitus when administered shortly after exposure to extreme levels of sound. Alteration of the fluorophenyl and carbamate functionalities present in the parent compound resulted in the synthesis of a small library of compounds with the goal of improving potency and selectivity for the Kv7.2/3 potassium ion channels. In vivo and in vitro testing is underway to determine efficacy.
The second part of this thesis describes efforts to develop and improved route to XJB-5-131, a truncated Gramicidin S-derived peptide designed to control reactive oxygen species (ROS) production in mitochondria. A new route to XJB-5-131 was explored utilizing a stereoselective α-alkenylation protocol and starting from vinyl boronic acids.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Reed, NicholasNLR22@pitt.eduNLR22
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Committee MemberDeiters, Alexanderdeiters@pitt.eduDEITERS
Date: 9 January 2015
Date Type: Publication
Defense Date: 18 November 2014
Approval Date: 9 January 2015
Submission Date: 1 December 2014
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 121
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: retigabine, tinnitus, Kv7, potassium ion channels, MMS-350, alkenylation, XJB-5-131, mitochondria, reactive oxygen species, organocatalysis
Date Deposited: 09 Jan 2015 20:39
Last Modified: 15 Nov 2016 14:25


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