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Synthesis and Cytotoxicity Studies of Fluorinated Derivatives of Vanadocene Y

2009; Wiley; Volume: 2009; Issue: 19 Linguagem: Inglês

10.1002/ejic.200900297

1099-0682

Brendan Gleeson, James Claffey, A. Deally, Megan Hogan, L.M.M. Mendez, Helge Müller‐Bunz, Siddappa A. Patil, Denise Wallis, Matthias Tacke,

Metal-Catalyzed Oxygenation Mechanisms

Abstract From the reaction of 6‐(2‐fluoro‐4‐methoxyphenyl)fulvene ( 1a ), 6‐(3‐fluoro‐4‐methoxyphenyl)fulvene ( 1b ) and 6‐[4‐(trifluoromethoxy)phenyl]fulvene ( 1c ) with LiBEt 3 H, lithiated cyclopentadienide intermediates ( 2a – c ) were synthesised. These intermediates were then transmetallated to vanadium with VCl 4 to yield the benzyl‐substituted vanadocenes bis[(2‐fluoro‐4‐methoxybenzyl)cyclopentadienyl]vanadium(IV) dichloride ( 3a ), bis[(3‐fluoro‐4‐methoxybenzyl)cyclopentadienyl]vanadium(IV) dichloride ( 3b ), and bis[(4‐trifluoromethoxybenzyl)cyclopentadienyl]vanadium(IV) dichloride ( 3c ). The three vanadocenes 3a – c were characterised by single‐crystal X‐ray diffraction. All three vanadocenes had their cytotoxicity investigated through MTT‐based preliminary in‐vitro testing on the LLC‐PK and Caki‐1 cell lines in order to determine their IC 50 values. Vanadocenes 3a – c were found to have IC 50 values of 6.0 (+/–4), 35 (+/–7) and 13 (+/–3) μ M on the LLC‐PK cell line and IC 50 values of 78 (+/–11), 18 (+/–16) and 2.2 (+/–0.5) μ M on the Caki‐1 cell line respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)