Lavendamycin, a naturally occurring quinoline-5,8-dione, has been shown to have anti-tumor properties by binding to the NAD(P)H:quinone oxidoreductase 1 (NQO1) enzyme which is over expressed in many cancer cells. The quinoline-5,8-dione ring is reduced to the corresponding diol which is cytotoxic. The over expression of the NQO1 enzyme in cancer cells made it a good target for bioreductive drug therapy. The focus of the project is to improve selectivity, activity, aqueous solubility, and cytotoxicity towards non-cancerous cells by altering the reactivity of the C2 position of the core quinoline-5,8-dione ring.  The isoxazoline and isoxazole rings are synthesized via a 1,3-dipolar cycloaddition using a nitrile oxide as the 1,3-dipole and a terminal alkene or alkyne as the dipolarophile.  Variation of the alkene and alkyne dipolarophiles, which are readily available, allows one to significantly alter the target molecule.

Synthesis of quinoline-5,8-dione derivatives

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.