Analogues of cytotoxic squamocin using reliable reactions: new insights into the reactivity and role of the α,β-unsaturated lactone of the annonaceous acetogenins

A small library of squamocin analogues has been prepared and screened biologically (cytotoxicity, inhibition of mitochondrial complex I and complex III). To centre diversity on a crucial part of the molecule (i.e., the α,β-unsaturated lactone), an original and reliable lactone opening reaction has b...

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Bibliographic Details
Published in:Tetrahedron 2006-06, Vol.62 (26), p.6248-6257
Main Authors: Duval, Romain A., Poupon, Erwan, Romero, Vanessa, Peris, Eva, Lewin, Guy, Cortes, Diego, Brandt, Ulrich, Hocquemiller, Reynald
Format: Article
Language:English
Subjects:
Annonaceous acetogenins
Chemistry in water
Click chemistry
Diels–Alder
Squamocin
Unsaturated lactone
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Summary:A small library of squamocin analogues has been prepared and screened biologically (cytotoxicity, inhibition of mitochondrial complex I and complex III). To centre diversity on a crucial part of the molecule (i.e., the α,β-unsaturated lactone), an original and reliable lactone opening reaction has been discovered and exploited among other efficient reactions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.04.066