Synthesis and Cytotoxicity Studies of Fluorinated Derivatives of Vanadocene Y

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 LiBEt3H, lithiated cyclopentadienide intermediates (2a–c) were synthesised. These intermediates were then transmetallated to vanadium with VCl4...

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Bibliographic Details
Published in:European Journal of Inorganic Chemistry 2009-07, Vol.2009 (19), p.2804-2810
Main Authors: Gleeson, Brendan, Claffey, James, Deally, Anthony, Hogan, Megan, Méndez, Luis Miguel Menéndez, Müller-Bunz, Helge, Patil, Siddappa, Wallis, Denise, Tacke, Matthias
Format: Article
Language:English
Subjects:
Antitumor agents
Cancer
Cytotox­icity
Drug design
Drug discovery
Fluorinated ligands
Hydridolithiation
Sandwich complexes
Vanadium
Vanadocene
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Summary: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 LiBEt3H, lithiated cyclopentadienide intermediates (2a–c) were synthesised. These intermediates were then transmetallated to vanadium with VCl4 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 IC50 values. Vanadocenes 3a–c were found to have IC50 values of 6.0 (+/–4), 35 (+/–7) and 13 (+/–3) μM on the LLC‐PK cell line and IC50 values of 78 (+/–11), 18 (+/–16) and 2.2 (+/–0.5) μM on the Caki‐1 cell line respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Within, the syntheses of three fluorinated derivatives of the p‐methoxybenzyl‐substituted vanadocene dichloride, through the hydridolithiation reaction of appropriatelyfluoro‐substituted fulvenes with LiBEt3H, are reported along with structural discussion. Additionally, these compounds were tested for their anticancer activity.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.200900297