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Glycol Methyl Ether and Glycol Amine Substituted Titanocenes as Antitumor Agents
Author(s) -
Strohfeldt Katja,
MüllerBunz Helge,
Pampillón Clara,
Sweeney Nigel J.,
Tacke Matthias
Publication year - 2006
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.200600586
Subject(s) - fulvene , chemistry , cyclopentadienyl complex , moiety , medicinal chemistry , ether , titanium , hydrolysis , amine gas treating , organic chemistry , catalysis
6‐[4‐(2‐Methoxyethoxy)phenyl]fulvene ( 3a ) and 6‐{4‐[2‐(dimethylamino)ethoxy]phenyl}fulvene ( 3b ) were prepared as the starting materials for the synthesis of three different classes of titanocenes, which are ansa ‐titanocenes, diarylmethyl‐substituted titanocenes and benzyl‐substituted titanocenes. Because the synthetic possibilities seem to be limited, only ansa ‐titanocene {1,2‐bis(cyclopentadienyl)‐1,2‐bis[4‐(2‐methoxyethoxy)phenyl]ethanediyl}titanium dichloride ( 4a ) and benzyl‐substituted titanocene bis‐{[4‐(2‐methoxyethoxy)benzyl]cyclopentadienyl}titanium(IV) dichloride ( 6a ) were obtained and characterised. The change in the substitution pattern of the phenyl moiety from an oxygen atom to a nitrogen atom had such a big influence on the reaction that not one compound of the three titanocene classes could be synthesised, and it was also not possible to obtain diarylmethyl‐substituted titanocenes with the use of either of the fulvenes. When benzyl‐substituted titanocene 6a was tested against pig kidney cells (LLC‐PK), an antiproliferative effect that results in an IC 50 value of 43 μ M , was observed. This IC 50 value is in the lower range of the cytotoxicities evaluated for titanocenes up to now. ansa ‐Titanocene 4a surprisingly showed, when tested on the same cell line, a proliferative effect together with a fast rate of hydrolysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)