Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

Abstract

In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms. [reaction: see text].

• Authors: Xin Jiang, Noelle Williams, Jef K De Brabander
• Journal: Organic letters (Org Lett) Vol. 9 Issue 2 Pg. 227-30 (Jan 18 2007) ISSN: 1523-7060 [Print] United States
• PMID: 17217271 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Coumarins
• Pyrans
• Pyrones
• mycalamide B
• psymberin
• psympederin
• mycalamide A
• pederin

Topics

• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Coumarins
• Drug Screening Assays, Antitumor
• Humans
• Magnetic Resonance Spectroscopy
• Models, Molecular
• Molecular Conformation
• Pyrans (chemical synthesis, chemistry, pharmacology)
• Pyrones (chemical synthesis, chemistry, pharmacology)
• Sensitivity and Specificity
• Structure-Activity Relationship