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dc.contributor.authorPigeon, Pascal
dc.contributor.authorGörmen, Meral
dc.contributor.authorKowalski, Konrad
dc.contributor.authorMüller-Bunz, Helge
dc.contributor.authorMcGlinchey, Michael J.
dc.contributor.authorTop, Siden
dc.contributor.authorJaouen, Gérard
dc.description.abstractIn the course of the preparation of a series of ferrocenyl derivatives of diethylstilbestrol (DES), in which one of the 4-hydroxyphenyl moieties was replaced by a ferrocenyl group, the McMurry reaction of chloropropionylferrocene with a number of mono-aryl ketones unexpectedly yielded the hydroxylated ferrocenyl DES derivatives, 5a–c, in poor yields (10%–16%). These compounds showed high activity on the hormone-independent breast cancer cell line MDA-MB-231 with IC50 values ranging from 0.14 to 0.36 µM. Surprisingly, non-hydroxylated ferrocenyl DES, 4, showed only an IC50 value of 1.14 µM, illustrating the importance of the hydroxyethyl function in this promising new series. For comparison, McMurry reactions of the shorter chain analogue chloroacetylferrocene were carried out to see the difference in behaviour with mono-aryl ketones versus a diaryl ketone. The effect of changing the length of the alkyl chain adjacent to the phenolic substituent of the hydroxylated ferrocenyl DES was studied, a mechanistic rationale to account for the unexpected products is proposed, and the antiproliferative activities of all of these compounds on MDA-MB-231 cells lines were measured and compared. X-ray crystal structures of cross-coupled products and of pinacol-pinacolone rearrangements are reported.pl_PL
dc.description.sponsorshipThe authors wish to thank P. Herson and J. Vaissermann for three crystal structure determinations and T. Cresteil for IC50 determinations. We thank Anh N’Guyen for full discussions. K.K.’s stay in Paris was supported through an European Community Marie Curie Fellowship (HMPT-CT-2000- 00186). We thank the Agence Nationale de la Recherche for financial support (ANR 2010 BLAN 7061 blanc “Mecaferrol”) and the Ministère des Affaires Etrangères for a doctoral fellowship (M.G.).pl_PL
dc.rightsUznanie autorstwa 3.0 Polska*
dc.subjectpinacol rearrangementpl_PL
dc.subjectMcMurry reactionpl_PL
dc.subjectantiproliferative activitypl_PL
dc.titleAtypical McMurry Cross-Coupling Reactions Leading to a New Series of Potent Antiproliferative Compounds Bearing the Key [Ferrocenyl-Ene-Phenol] Motifpl_PL
dc.contributor.authorAffiliationChimie ParisTech, 11 rue Pierre et Marie Curiepl_PL
dc.contributor.authorAffiliationSorbonne Universitéspl_PL
dc.contributor.authorAffiliationUniversity of Łódź, Faculty of Chemistrypl_PL
dc.contributor.authorAffiliationUniversity College Dublinpl_PL
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dc.referencesX-ray data for 14: The unit cell is orthogonal with a = 9.8552(7) Å, b = 9.7478(8) Å, c = 18.523(2) Å, α = β = γ = 90°, V = 1729.5(2) Å3, and the space group is Pnma (#62).pl_PL

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Uznanie autorstwa 3.0 Polska
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