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Novel benzyl-substituted molybdocene anticancer drugs

2010; Elsevier BV; Volume: 363; Issue: 8 Linguagem: Inglês

10.1016/j.ica.2010.02.020

1873-3255

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

Ferrocene Chemistry and Applications

From the reaction of 6-(p-methoxyphenyl) fulvene (1a), 6-(3,4-dimethoxyphenyl) fulvene (1b) and 6-(3,4,5-trimethoxyphenyl) fulvene (1c) with LiBEt3H, lithiated cyclopentadienide intermediates (2a–c) were synthesised. These intermediates were then transmetallated to molybdocene using MoCl4 (synthesized in situ) to yield the benzyl-substituted molybdocenes bis-[(p-methoxybenzyl)cyclopentadienyl] molybdenum (IV) dichloride (3a), bis-[(3,4-dimethoxybenzyl)cyclopentadienyl] molybdenum (IV) dichloride (3b), and bis-[(3,4,5-trimethoxybenzyl)cyclopentadienyl] molybdenum (IV) dichloride (3c). The molybdocene 3a was characterised by single crystal X-ray diffraction. All three molybdocenes 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 and compare them with the corresponding titanocene and vanadocene dichloride derivatives. Molybdocenes 3b–c were found to have the same IC50 values of 290 μM, while 3a yielded a value of 84 μM, respectively