Literature DB >> 19750529

Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76.

Lin Dong1, Heiko Schill, Rebecca L Grange, Achim Porzelle, Jenny P Johns, Peter G Parsons, Victoria A Gordon, Paul W Reddell, Craig M Williams.   

Abstract

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.

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Year:  2009        PMID: 19750529     DOI: 10.1002/chem.200901525

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

1.  Rapid total syntheses utilizing "supersilyl" chemistry.

Authors:  Brian J Albert; Yousuke Yamaoka; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-08       Impact factor: 15.336

2.  Blind trials of computer-assisted structure elucidation software.

Authors:  Arvin Moser; Mikhail E Elyashberg; Antony J Williams; Kirill A Blinov; Joseph C Dimartino
Journal:  J Cheminform       Date:  2012-02-09       Impact factor: 5.514

3.  Enantioselective Total Synthesis of (+)-EBC-23, a Potent Anticancer Agent from the Australian Rainforest.

Authors:  Arun K Ghosh; Che-Sheng Hsu
Journal:  J Org Chem       Date:  2021-04-19       Impact factor: 4.354

  3 in total

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