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. 2021 Jul 23;11(39):24282-24291.
doi: 10.1039/d1ra04943g. eCollection 2021 Jul 6.

Boron-containing capsaicinoids

Jennifer A Melanson  1 , Maxim F Landry  1 , Martin Lanteigne  2 , Katherine McQuillan  2 , Hebelin Correa  2 , Russell G Kerr  3 , Stephen A Westcott  1
Affiliations

Boron-containing capsaicinoids

Jennifer A Melanson et al. RSC Adv. .

Abstract

This study reports on the preparation of eight new boron-containing capsaicinoids bearing long aliphatic chains, as an expansion of our previous studies to include tertiary amide derivatives into our substrate scope. Our boron-moiety, a pinacolboronate ester (Bpin) fragment, has been incorporated in two locations: as an aryl substituent of the capsaicinoid produced by the reductive amination of veratraldehyde, or at the terminal end of an aliphatic substituent using an iridium catalyzed hydroboration reaction. We report that most compounds in our series show moderate antimicrobial and cytotoxic activity, surpassing activities noted in our previous study.

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Conflict of interest statement

There are no conflicts of interest to declare.

Figures

Fig. 1
Fig. 1. FDA approved organoboron compounds.
Fig. 2
Fig. 2. Capsaicin and biologically active capsaicinoids.
Scheme 1
Scheme 1. Synthesis of boron-containing capsaicinoids.
See this image and copyright information in PMC

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