Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 20, Issue 11, Pages 3635-3651Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2012.03.059
Keywords
Goniothalamin; Cancer cells; Antiproliferative activity; gamma-Pyrones; Dihydro-gamma-pyrones; Aza-goniothalamin
Funding
- FAPESP [10/16990-1, 2009/51602-5]
- CNPq
- Capes
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [10/16990-1] Funding Source: FAPESP
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The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.
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