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Natural Sciences Seminar
Friday, March 1, 2019,4:00 pm - 5:00 pm EST
Ralph N. Salvatore, Ph.D., associate professor of chemistry at Southeastern University in Lakeland, will present “Cesium Effect: Mild Efficient Formation of Carbon-Heteroatom Bonds and Synthesis towards Cancer Therapeutics, Antivirals, and Parkinson’s Disease Metabolites.”
Cesium reagents are well known catalysts for a wide variety of synthetic transformations and the generation of pharmaceutically useful intermediates. In particular, cesium bases are generally far superior to their alkali metal counterparts with respect to decrease in reaction time and an increase in product yields. In addition, cesium salts have excelled at controlling reaction chemoselectivity and are highly compatible with a wide range of functional groups. This enhanced reactivity conducted under mild reaction conditions, is commonly known as the “cesium effect.” This effect, which is marked by increased salt solubility and the generation of highly reactive “naked anions”, leads to striking efficiency and versatility in alkylation reactions. However, the exact cause of this effect, to date, is still under investigation.
The first portion of this seminar will provide an overview of synthetic methodologies for numerous cesium base promoted alkylation reactions developed in our laboratories for the construction of a plethora of carbon-heteroatom bonds in both solution phase and on solid support. Second, utilizing our subsequent protocols, the synthesis of various macrocyles, heterocycles, supramolecular compounds, oligionucleotides and novel artificial biomolecules will be discussed. In particular, since we are interested in disrupting protein-protein interaction, we have designed small peptidomimetic molecules in order to bind strongly to the targeted proteins, hoping that these new molecules can replace the natural binding proteins. Such efforts have been directed toward the preparation of structurally diverse artificial biomolecules using the carbonate or carbamate moiety as the backbone (oxapeptoids and “carbamatoids,” respectively), the dithiocarbamate, diothiocarbonate, diselenocarbamate, diseleneocabonate and similar scaffolds containing isothiocyanates, cyanates, similar derivatives, hydrazine moieties or the secondary amine as the bridge to induce apoptosis.
Additional synthetic applications toward other small molecules, DOPAL, an important metabolite of the major brain neurotransmitter, namely dopamine as well as the design of a non-nucleoside inhibitor of HIV-1 reverse transcriptase inhibitor will be shared. Thus, these procedures, we believe hold great promise for the development of numerous drug candidates to combat disease, which will help to advance organic synthesis, as well as to enhance the progress of related fields such as biology and medicinal chemistry.