Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76
| Autor: | Craig M. Williams, Jenny P. Johns, Achim Porzelle, Paul Reddell, Heiko Schill, Lin Dong, Peter G. Parsons, Rebecca L. Grange, Victoria A. Gordon |
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| Rok vydání: | 2009 |
| Předmět: |
Stereochemistry
Mice Nude Stereoisomerism Antineoplastic Agents Rainforest Catalysis Mice Acetals DU145 Cell Line Tumor Animals Humans Spiro Compounds Structural motif Cinnamomum Pyrans biology Chemistry Organic Chemistry Cinnamomum laubatii Australia Total synthesis General Chemistry biology.organism_classification Xenograft Model Antitumor Assays respiratory tract diseases Fruit Tropical rainforest |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 15(42) |
| ISSN: | 1521-3765 |
| Popis: | EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8 % overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze-Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults. |
| Databáze: | OpenAIRE |
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