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Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues
Bhaskar C Das1, Sakkarapalayam M Mahalingam, Todd Evans
1Department of Nuclear Medicine, Albert Einstein College of Medicine, Bronx, NY 10461, USA.
Abstract:
We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (t)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators of TGF-beta signaling pathways.
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