Georgia Southern University Digital Commons@Georgia Southern Electronic Theses and Dissertations Graduate Studies, Jack N. Averitt College of Summer 2017 Synthesis and Biological Activity of Novel Tu100 Derivatives Oladotun J. Alao Follow this and additional works at: https://digitalcommons.georgiasouthern.edu/etd Part of the Medicinal-Pharmaceutical Chemistry Commons, and the Organic Chemistry Commons Recommended Citation Alao, Oladotun J., "Synthesis and Biological Activity of Novel Tu100 Derivatives" (2017). Electronic Theses and Dissertations. 1617. https://digitalcommons.georgiasouthern.edu/etd/1617 This thesis (open access) is brought to you for free and open access by the Graduate Studies, Jack N. Averitt College of at Digital Commons@Georgia Southern. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of Digital Commons@Georgia Southern. For more information, please contact
[email protected]. SYNTHESIS AND BIOLOGICAL ACTIVITY OF NOVEL TU100 DERIVATIVES by OLADOTUN JOHN-PAUL ALAO (Under the direction of John DiCesare) ABSTRACT In an attempt to create more effective chemotherapeutic compounds, the naphthoquinone adduct, 12,13-dihydro-N-methyl-6,11,13-trioxo-5H-benzo[4,5]cyclohepta [1,2 b]naphthalen-5,12-imine (hereafter called TU100) was synthesized. Inspired by its unique and novel mechanism of action, a series of structural derivatives were synthesized to explore structure-activity relationships. The analogues exhibited different cytotoxicity profiles, revealing the indicated regions are involved in cell death induction. Furthermore, the analogues had dramatically different effects on cellular ATP production, suggesting different molecular targets. Synthesis, biological activity, and SAR study of these analogues will be revealed. INDEX WORDS: TU100, Benzoquinone adduct, GSU100, Anthraquinone adduct, N-ethyl naphthoquinone adduct, p-Phenylbenzoquinone adduct, Cancer, Antitumor activity SYNTHESIS AND BIOLOGICAL ACTIVITY OF NOVEL TU100 DERIVATIVES by OLADOTUN JOHN-PAUL ALAO B.