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Synthesis and Cytotoxicity Studies of New (Dimethylamino)-Functionalised and 7-Azaindole-Substituted ‘Titanocene’ Anticancer Agents (7-Azaindole=1H-Pyrrolo[2,3-b]pyridine)

✍ Scribed by Megan Hogan; Juliet Cotter; James Claffey; Brendan Gleeson; Denise Wallis; Donal O'Shea; Matthias Tacke

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
340 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

From the carbolithiation of 1‐(cyclopenta‐2,4‐dien‐1‐ylidene)‐N,N‐dimethylmethanamine (=6‐(dimethylamino)fulvene; 3) and different lithiated azaindoles 2 (1‐methyl‐7‐azaindol‐2‐yl, 1‐[(diethylamino)methyl]‐7‐azaindol‐2‐yl, and 1‐(methoxymethyl)‐7‐azaindol‐2‐yl), the corresponding lithium cyclopentadienide intermediates 4a–4c were formed (7‐azaindole=1__H__‐pyrrolo[2,3‐b]pyridine). The latter underwent a transmetallation reaction with TiCl~4~ resulting in the (dimethylamino)‐functionalised ‘titanocenes’ 5a–5c. When the ‘titanocenes’ 5a–5c were tested against LLC‐PK cells, the IC~50~ values obtained were of 8.8, 12, and 87 μM, respectively. The most cytotoxic ‘titanocene’, 5a, with an IC~50~ value of 8.8 μM is nearly as cytotoxic as cis‐platin, which showed an IC~50~ value of 3.3 μM when tested on the epithelial pig kidney LLC‐PK cell line, and ca. 200 times better than ‘titanocene dichloride’ itself.

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