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Issue 1, 2017
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Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring

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Abstract

The preparation of several new analogues of the natural dihydropyrone pironetin is described. They differ from the natural product mainly in the nature of the side chain and the lactone ring. Their cytotoxic activity has been measured. In addition, their interaction with tubulin, their ability to inhibit the secretion of the vascular endothelial growth factor (VEGF) and the expression of angiogenesis and telomerase-related genes have been determined. Unexpectedly, and unlike pironetin, the lactones studied in this work do not interact with tubulin. Two of the compounds have been found to downregulate the expression of the hTERT and VEGF genes. Furthermore, one of them causes an appreciably decrease in the secretion of the VEGF protein.

Graphical abstract: Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring

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Publication details

The article was received on 25 Jul 2016, accepted on 21 Nov 2016 and first published on 22 Nov 2016


Article type: Paper
DOI: 10.1039/C6OB01585A
Org. Biomol. Chem., 2017,15, 220-232

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    Synthesis and biological evaluation of simplified pironetin analogues with modifications in the side chain and the lactone ring

    S. Roldán, A. Cardona, L. Conesa, J. Murga, E. Falomir, M. Carda and J. A. Marco, Org. Biomol. Chem., 2017, 15, 220
    DOI: 10.1039/C6OB01585A

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