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The synthesis and cytotoxic evaluation of a series of benzodioxole substituted titanocenes

✍ Scribed by Nigel J. Sweeney; James Claffey; Helge Müller-Bunz; Clara Pampillón; Katja Strohfeldt; Matthias Tacke

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
243 KB
Volume
21
Category
Article
ISSN
0268-2605

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✦ Synopsis

Abstract

Using 6‐benzo[1,3]dioxolefulvene (1a), a series of benzodioxole substituted titanocenes was synthesized. The benzyl‐substituted titanocene bis[(benzo[1,3]dioxole)‐5‐methylcyclopentadienyl] titanium (IV) dichloride (2a) was synthesized from the reaction of Super Hydride with 1a. An X‐ray determined crystal structure was obtained for 2a. The ansa‐titanocene {1,2‐di(cyclopentadienyl)‐1,2‐di‐(benzo[1,3]dioxole)‐ethanediyl} titanium(IV) dichloride (2b) was synthesized by reductive dimerisation of 1a with titanium dichloride. The diarylmethyl substituted titanocene bis(di‐(benzo[1,3]dioxole)‐5‐methylcyclopentadienyl) titanium(IV) dichloride (2c) was synthesized by reacting 1a with the para‐lithiated benzodioxole followed by transmetallation with titanium tetrachloride. When titanocenes 2a–c were tested against pig kidney (LLC‐PK) cells inhibitory concentrations (IC~50~) of 2.8 × 10^−4^, 1.6 × 10^−4^ and 7.6 × 10^−5^ M, respectively, were observed. These values represent improved cytotoxicity against LLC‐PK, when compared with unsubstituted titanocene dichloride, but are not as impressive as values obtained for titanocenes previously synthesized using the above methods. Copyright © 2006 John Wiley & Sons, Ltd.

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