Issue 23, 2009
From the journal:

Organic & Biomolecular Chemistry

Evaluation of the pharmacophoric motif of the caged Garciniaxanthones†

Oraphin Chantarasriwong,ab   Woo Cheal Cho,a   Ayse Batova,*c   Warinthorn Chavasiri,b   Curtis Moore,a   Arnold L. Rheingolda  and  Emmanuel A. Theodorakis*a  

* Corresponding authors

a Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive MC: 0358, La Jolla, USA
E-mail: etheodor@ucsd.edu
Fax: +1-858-822-0386
Tel: +1-858-822-0456

b Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Thailand

c Department of Pediatrics/Hematology-Oncology, UC San Diego, 200 West Arbor Drive, San Diego, USA

Abstract

The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garciniaxanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols that, together with a Claisen/Diels–Alder reaction cascade, provides rapid and efficient access to various caged analogues. Evaluation of the growth inhibitory activity of these compounds leads to the conclusion that the intact ABC ring system containing the C-ring caged structure is essential to the bioactivity. Studies with cluvenone (7) also showed that these compounds induce apoptosis and exhibit significant cytotoxicity in multidrug-resistant leukemia cells. As such, the caged Garciniaxanthone motif represents a new and potent pharmacophore.

Graphical abstract: Evaluation of the pharmacophoric motif of the caged Garciniaxanthones

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Article information

DOI
https://doi.org/10.1039/B913496D
Article type
Paper
Submitted
08 Jul 2009
Accepted
28 Aug 2009
First published
24 Sep 2009

Org. Biomol. Chem., 2009,7, 4886-4894

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Evaluation of the pharmacophoric motif of the caged Garciniaxanthones

O. Chantarasriwong, W. C. Cho, A. Batova, W. Chavasiri, C. Moore, A. L. Rheingold and E. A. Theodorakis, Org. Biomol. Chem., 2009, 7, 4886 DOI: 10.1039/B913496D

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