Electrochemical Reduction of Arylsulfonyl Indoles

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He, Yimeng
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University of Guelph

The indole framework has been recognized as a biologically important pharmacophore with a vast array of pharmacological effects and therapeutic applications. The N-arylsulfonyl indole derivatives, particularly the nitro-substituted arylsulfonyl indoles, are emerging as candidates as novel HIV-1 inhibitors. The electroactive nature of indole and its ability to generate radicals have been attributed to some of its observed pharmacological effects; in this regard the indolic radicals have received wide attention. In this thesis, a series of arylsulfonyl indoles was successfully synthesized. These compounds were subjected to electrochemical studies in an attempt to investigate their susceptibilities to reduction, the nature of the initial electron transfer mechanism, the potential bond dissociation, as well as any potential dependence on the nature of the substituent. Many aspects of the thesis are built upon the foundation laid out by the past studies on the electrochemical reduction of arylsulfonyl chlorides and arylsulfonyl phthalimides, by previous members of the Houmam group. In this regard the study also served as a further investigation of the fundamental aspects of electron transfer to organic molecules in general and to arylsulfonyl derivatives in particular. Data was compared with previously-investigated and structurally-related compounds such as arylsulfonyl chlorides and arylsulfonyl phthalimides.

Electrochemistry, Electrochemical Reduction, Dissociative Electron Transfer, Arylsulfonyl Indole