New Excursions Into the Synthesis and Medicinal Chemistry of the Disulfide Bond

Abstract

The presentation discusses two themes of current interest in my research group in conjunction with a garlic mimics program. The first involves a new one-pot methodology for preparing unsymmetrical disulfides in high yield using 1-chlorobenzotriazole (BtCl) as oxidant, which can be applied to a range of functional types. The second part of the lecture will discuss the synthesis of derivatives of the garlic-derived natural product ajoene, in conjunction with an anti-cancer screening program. The synthesis has been used to prepare a fluorescently tagged derivative of the natural product that has been used to investigate localization and mode of action within the cancer cell using confocal laser scanning microscopy.

GRAPHICAL ABSTRACT

Keywords:

• Disulfide
• heterodisulfide synthesis methodology
• ajoene
• cancer
• fluorescently tagged
• CLSM
• ER and mitochondrial stress

Acknowledgments

This work was supported by the South African Research Chairs Initiative (SARCHI) of the Department of Science and Technology, the National Research Foundation (NRF), and research grants from the Medical Research Council (MRC) of South Africa and the University of Cape Town.

Notes

*This article was submitted as part of the Special Issue dedicated to the 25th International Conference on the Organic Chemistry of Sulfur (ISOCS-25) which appears in Volume 188 Issue 4 of Phosphorus, Sulfur, and Silicon.