Abstract
From the carbolithiation of 6-N,N-dimethylaminofulvene (3a) and different lithiated heterocycles (5-N-methylpyrazolyl, 2-thiazolyl, and 2-N(N,N-dimethylamino)methylimidazolyl), the corresponding lithium cyclopentadienide intermediate (4a−c) was formed. These three lithiated intermediates underwent a transmetalation reaction with TiCl4, resulting in dimethylamino-functionalized titanocenes 5a−c. When these titanocenes were tested against LLC-PK cells, the IC50 values obtained were 53 and 61 μM for titanocenes 5a and 5b, respectively. The most cytotoxic titanocene in this paper (5c), with an IC50 value of 5.4 μM, is found to be almost as cytotoxic as cisplatin, which showed an IC50 value of 3.3 μM, when tested on the epithelial pig kidney LLC-PK cell line, and titanocene 5c is approximately 400 times more active than titanocene dichloride itself.
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