Novel Achiral Aryl‐Substituted Vanadocenes: Synthesisand Preliminary Cytotoxicity Studies
Brendan Gleeson A B , Anthony Deally A , Helge Müller‐Bunz A , Siddappa Patil A and Matthias Tacke A BA Conway Institute of Biomolecular and Biomedical Research, Centre for Synthesisand Chemical Biology (CSCB), UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
B Corresponding authors. Email: matthias.tacke@ucd.ie, brendan.gleeson@ucd.ie
Australian Journal of Chemistry 63(11) 1514-1520 https://doi.org/10.1071/CH10196
Submitted: 13 May 2010 Accepted: 21 October 2010 Published: 11 November 2010
Abstract
From the reaction of 6‐(4‐methoxymethyl‐phenyl) fulvene (1a), 6‐(N‐methyl‐pyrrole) fulvene (1b), and 6‐(4‐dimethylamino‐phenyl) fulvene (1c) with LiBEt3H, the corresponding lithium cyclopentadienide intermediates (2a–c) were synthesized. These intermediates were then transmetallated to vanadium with VCl4 to yield the substituted vanadocene dichlorides bis‐[(4‐methoxymethyl‐benzyl)cyclopentadienyl] vanadium(iv) dichloride (3a), bis‐[(N‐methylpyrrole)2‐methylcyclopentadienyl] vanadium(iv) dichloride (3b), and bis‐[(p‐dimethylaminobenzyl)cyclopentadienyl] vanadium(iv) dichloride (3c). The vanadocene dichloride 3a was characterized by single crystal X‐ray diffraction. All three vanadocenes had their cytotoxicity investigated through MTT based preliminary in vitro testing on the human renal cell line Caki‐1 in order to determine their IC50 values. Vanadocenes 3a–b were found to have IC50 values of 6.5 and 5.2 µM, respectively, while 3c displayed a superior value of 1.7 µM.
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