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Multi-gram total syntheses of Zapotin and ()-Abyssinone II, cancer chemopreventive natural products. Maiti, Arup; Pezzuto, John M.; Cuendet, Muriel; Kondratyuk, Tamara; Croy, Vicki L.; Cushman, Mark. Department of Medicinal Chemistry and Molecular Pharmacology and The Purdue Cancer Center, Purdue University, West Lafayette, IN, USA. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006 (2006), MEDI-172. Publisher: American Chemical Society, Washington, D. C CODEN: 69IHRD Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2006:861627 CAPLUS

Abstract

Zapotin (1) and abyssinone II (2) are two natural products found in the edible plants Casimiroa edulis and Broussonetia papirifera, resp. Very recently zapotin was evaluated in HL-60 cell differentiation (ED50 = 0.5 .mu.M) and mouse mammary organ culture model (MMOC) assays and abyssinone II was evaluated in the aromatase assay (IC50 = 0.4 .mu.M). Both of these natural products were found to be very active as cancer chemopreventive and chemotherapeutic agents. Based on these results, novel LiHMDS-mediated, cost efficient, multi-gram total syntheses of both natural products were carried out. The synthetic zapotin was active in TPA-induced ornithine decarboxylase (ODC, IC50 = 1.9 .mu.M) and inhibition of NF-.kappa.B (IC50 = 16.4 .mu.M) screening assays. Several structurally modified analogs of abyssinone II were synthesized and a structure-activity (SAR) model was established to search for new potent chemopreventive agents. (Supported by program project grant P01 CA48112 funded by the NCI).