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Tuesday, April 24 • 12:00pm - 1:30pm
Synthesis Of Novel Carbazole Analogs And Evaluation Of Their Cytotoxicity

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Carbazoles are aromatic heterocyclic compounds that contain similar core compound structure and functional groups as Combretastatin A-4 and colchicine which are tubulin-inhibiting anticancer drugs. Tubulin inhibitors function as antimitotic agents by arresting the growth cycle of cancer cells. Carbazoles have exhibited cytotoxicity of cancer cells by the inhibition of DNA topoisomerase II through intercalation of DNA and the formation of covalent adducts. With the application of carbazoles as rather new anticancer drugs, there are opportunities to investigate the effects of various moieties within the drug, namely electron-withdrawing and electron-donating, on the efficiency of cytotoxicity via Methylthiazol Tetrazolium Assay (MTT). The carbazole analogs will be synthesized in a series of steps involving a substitution reaction and an Aldol condensation to yield the 3,4,5-trimethoxyphenyl vinyl azide ester. The second ring closure to form the indole will be performed by thermal cyclization of the vinyl azide. Finally, a Wittig reaction followed by 6π electrocyclization will close the third ring where variable nucleophilic aromatic substitutions will occur. These carbazole analogs will have the 3,4,5-trimethoxyphenyl group and two biaryl rings of Combretastatin A-4 and colchicine and thus, can be examined for anti-tubulin activity.


Tuesday April 24, 2018 12:00pm - 1:30pm PDT
Sherrill Center Concourse