C8c–C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties

doi:10.1016/j.bmcl.2005.09.032

Bioorganic & Medicinal Chemistry Letters

Volume 16, Issue 1, 1 January 2006, Pages 181-185

https://doi.org/10.1016/j.bmcl.2005.09.032 Get rights and content

Abstract

Four enantiomerically pure monoseco-analogues, 5, 7, 9, and 11, of the phenanthroquinolizidine alkaloid julandine (1) and four of congener cryptopleurine (2), viz. compounds 6, 8, 10, and 12, have been prepared and subjected to preliminary biological evaluation. These analogues show dramatically reduced cytotoxicity compared with the parent system 2 but they are, nevertheless, potent anti-angiogenic agents.

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Acknowledgments

We thank the Institute of Advanced Studies for financial support including the provision of a Ph D Scholarship to MOS. Dr. Paul Savage of CSIRO Molecular Science (Melbourne) is thanked for providing an authentic sample of the natural product cryptopleurine (2).

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C8c–C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties

Abstract

Graphical abstract

Section snippets

Acknowledgments

Aust. J. Chem.

J. Chem. Soc., Chem. Commun.

Chem. Aust.

Aust. J. Chem.

Aust. J. Chem.

Aust. J. Chem.

Synthesis

J. Org. Chem.

J. Nat. Prod.

Cancer Res.

Tetrahedron

An. Quim.

Chem. Abstr.

An. Quim.

Chem. Abstr.

J. Heterocycl. Chem.

J. Heterocycl. Chem.

Tetrahedron

J. Heterocycl. Chem.

Synth. Commun.

Nat. Prod. Rep.