Boron-containing capsaicinoids

Melanson, Jennifer A.; Landry, Maxim F.; Lanteigne, Martin; McQuillan, Katherine; Correa, Hebelin; Kerr, Russell G.; Westcott, Stephen A.

doi:10.1039/d1ra04943g

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2023

2024

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A comparative study of boron-containing and boron-omitted capsaicinoids

Ngô,

Park,

Stack

et al. 2024

Can. J. Chem.

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This study reports the synthesis and characterization of a limited number of novel boron-containing and boron-omitted capsaicinoids, providing 12 unique substrates. We have previously reported boron-containing capsaicinoids that showed improved bioactivity compared to capsaicin itself but have yet to test a series of analogous boron-omitted substrates as a direct comparison. The boron-containing capsaicinoids bear a pinacolboronate ester (Bpin) group, which was incorporated using an iridium-catalyzed hydroboration reaction. We report that although nearly all compounds display moderate cytotoxic activity that bests that of capsaicin against human colon HCT116 cancer cells, the activity of our boron-omitted capsaicinoids surpasses that of the boron-containing analogues.

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