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Synthesis of Apoptotic Spirooxindoles

Institution: Beckman Research Institute of the City of Hope
Investigator(s): Xiaoqing Han, Ph.D.
Award Cycle: 2007 (Cycle 16) Grant #: 16FT-0070 Award: $75,000
Subject Area: General Biomedical Science
Award Type: Postdoctoral Fellowship Awards

Initial Award Abstract
Based on data from the National Cancer Institute, cigarette smoking causes approximately 30 percent of all cancer-related deaths in the United States. In particular, smoking alone is responsible for 87 percent of lung cancer deaths. Despite the significant research and medical efforts devoted to the treatment of lung cancer, the five-year survival rate for patients diagnosed with lung cancer is only 14 percent. This is a sobering statistic and more effective treatments are urgently needed. Natural products play an important role in pharmaceutical development. Based on a recent report by the NCI, approximately 74 percent of the anti-cancer drugs on the market today are based on natural products and derivatives thereof. Natural products total synthesis provides not only a viable means to access necessary quantities for biological evaluation, but also an efficient way to access derivatives that have more potent or desirable properties. A growing number of indole- and spirooxindole-based alkaloids derived from tryptamine and/or tryptophan display significant anti-cancer activities. The research described herein is based on the development of new synthetic methodology for the construction of such alkaloids and their synthetic derivatives for biological testing. As a part of our ongoing research on the asymmetric construction of spiropyrrolidine oxindole alkaloids, a proposed synthesis of the traditional Chinese herbal metabolites rhynchophylline, isorhynchophylline, 17-demethoxyisorhynchophylline and related spirooxindole analogs is outlined. These and structurally related compounds have been used to treat various ailments, including cancer and have the potential for development as antineoplastic agents. The anti-cancer activities of these alkaloids will be examined through our ongoing interdisciplinary collaboration within the Comprehensive Cancer Center at the City of Hope National Medical Center. The development of the synthetic methodology for the synthesis of the aforementioned alkaloids and synthetic derivatives will be useful in identifying lead compounds for anti-cancer drug candidates.