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. 2014 Jul 17:10:1630-7.
doi: 10.3762/bjoc.10.169. eCollection 2014.

Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions

Andreas Gansäuer  1 , Andreas Okkel  1 , Lukas Schwach  1 , Laura Wagner  2 , Anja Selig  2 , Aram Prokop  3
Affiliations

Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions

Andreas Gansäuer et al. Beilstein J Org Chem. .

Abstract

An operationally simple, convenient, and mild strategy for the synthesis of triazole-substituted titanocenes via strain-driven 1,3-dipolar cycloadditions between azide-functionalized titanocenes and cyclooctyne has been developed. It features the first synthesis of titanocenes containing azide groups. These compounds constitute 'second-generation' functionalized titanocene building blocks for further synthetic elaboration. Our synthesis is modular and large numbers of the complexes can in principle be prepared in short periods of time. Some of the triazole-substituted titanocenes display high cyctotoxic activity against BJAB cells. Comparison of the most active complexes allows the identification of structural features essential for biological activity.

Keywords: azides; click-chemistry; cycloadditions; cytotoxicity; titanocenes.

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Figures

Scheme 1
Scheme 1
Modular titanocene synthesis via acylation reactions [24].
Figure 1
Figure 1
Carboxylates employed as titanocene starting materials for azide-substituted complexes.
Figure 2
Figure 2
Azides employed in this study and conditions for their synthesis.
Figure 3
Figure 3
Most active titanocenes of this study and their AC50 values.
See this image and copyright information in PMC

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