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Synthesis and Cytotoxicity Studies of Fluorinated Derivatives of Vanadocene Y
Author(s) -
Gleeson Brendan,
Claffey James,
Deally Anthony,
Hogan Megan,
Méndez Luis Miguel Menéndez,
MüllerBunz Helge,
Patil Siddappa,
Wallis Denise,
Tacke Matthias
Publication year - 2009
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200900297
Subject(s) - fulvene , chemistry , cyclopentadienyl complex , vanadium , cytotoxicity , medicinal chemistry , stereochemistry , catalysis , in vitro , organic chemistry , biochemistry
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)