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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Synthesis of boroxifen, a nido-carborane analogue of tamoxifen.

A nido-carborane analogue of tamoxifen, the widely employed breast cancer therapy agent, was prepared as an archetype of a potential new class of antiestrogen and boron neutron capture therapy agent in which the carborane is incorporated within the framework of the parent compound. The carborane was introduced through the reaction of 6,9-bis(acetonitrile)decaborane with a unique and highly conjugated ene-yne, which was prepared stereoselectively. NMR spectroscopy and a crystal structure of a key intermediate, the carborane analogue of chloro-tamoxifen, demonstrated the structural similarities between the tamoxifen carboranes and their corresponding phenyl analogues.[1]


  1. Synthesis of boroxifen, a nido-carborane analogue of tamoxifen. Valliant, J.F., Schaffer, P., Stephenson, K.A., Britten, J.F. J. Org. Chem. (2002) [Pubmed]
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