Selective Oxidation of Disulfide-Embedded Cyclic Amides
Document Type
Oral Presentation
Event Website
https://source2022.sched.com/
Start Date
18-5-2022
End Date
18-5-2022
Keywords
Organic Chemistry, Sulphur, organosulfur compounds, oxidation
Abstract
Organic compounds that contain sulfur (i.e., organosulfur compounds) are associated with rich flavors. Meanwhile, ~80% of small-molecule drugs contain a nitrogen atom and ~67% are found within a heterocycle. Specifically, N,S-heterocycles such as 4-thiazolidinones exhibit a diverse range of biological activities, including antifungal, antioxidant, cytotoxic, anti-inflammatory, anticonvulsant, anti-HIV, antitubercular, and many others. Organosulfur compounds are also present in several medicines, fragrances, and materials. A cost-effective and environmentally friendly method for the controlled synthesis of two types of organosulfur compounds; namely sulfoxides (one with two carbon-sulfur bonds and one sulfur-oxygen bond) and sulfones (one with two carbon-sulfur bonds and two sulfur-oxygen bonds) has been developed. The outcomes are achieved through controlled oxidation of cyclic compounds bearing a disulfide bridge (R-S-S-R) as well as a protein-type bond (referred to herein as disulfide-embedded lactams). The cost was controlled by using a cheap and commercially available catalyst known as N-fluorobenzenesulfonimide (NFSI). Water served as the solvent and the oxygen source for the controlled oxidation. Since water is a green and an environmentally friendly solvent, the successful execution of the proposed strategy has set the stage for the attainment of the highly coveted green chemistry status. A structure-activity relationship (SAR) study is being performed together with another group member and Dr. Dondji in the Department of Biological Sciences, with a focus on neglected tropical diseases, especially leishmaniasis.
Poster video presentation: https://www.youtube.com/watch?v=9O5HE44GcKY
Recommended Citation
Sax, McKenna, "Selective Oxidation of Disulfide-Embedded Cyclic Amides" (2022). Symposium Of University Research and Creative Expression (SOURCE). 94.
https://digitalcommons.cwu.edu/source/2022/COTS/94
Department/Program
Chemistry
Additional Mentoring Department
Chemistry
Additional Mentoring Department
Funding from Central OUR Grants
Selective Oxidation of Disulfide-Embedded Cyclic Amides
Organic compounds that contain sulfur (i.e., organosulfur compounds) are associated with rich flavors. Meanwhile, ~80% of small-molecule drugs contain a nitrogen atom and ~67% are found within a heterocycle. Specifically, N,S-heterocycles such as 4-thiazolidinones exhibit a diverse range of biological activities, including antifungal, antioxidant, cytotoxic, anti-inflammatory, anticonvulsant, anti-HIV, antitubercular, and many others. Organosulfur compounds are also present in several medicines, fragrances, and materials. A cost-effective and environmentally friendly method for the controlled synthesis of two types of organosulfur compounds; namely sulfoxides (one with two carbon-sulfur bonds and one sulfur-oxygen bond) and sulfones (one with two carbon-sulfur bonds and two sulfur-oxygen bonds) has been developed. The outcomes are achieved through controlled oxidation of cyclic compounds bearing a disulfide bridge (R-S-S-R) as well as a protein-type bond (referred to herein as disulfide-embedded lactams). The cost was controlled by using a cheap and commercially available catalyst known as N-fluorobenzenesulfonimide (NFSI). Water served as the solvent and the oxygen source for the controlled oxidation. Since water is a green and an environmentally friendly solvent, the successful execution of the proposed strategy has set the stage for the attainment of the highly coveted green chemistry status. A structure-activity relationship (SAR) study is being performed together with another group member and Dr. Dondji in the Department of Biological Sciences, with a focus on neglected tropical diseases, especially leishmaniasis.
Poster video presentation: https://www.youtube.com/watch?v=9O5HE44GcKY
https://digitalcommons.cwu.edu/source/2022/COTS/94
Faculty Mentor(s)
Timothy Beng