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.
Highlights
Organoboron compounds are beginning to receive wellwarranted attention in the pharmaceutical industry, including ve drugs recently approved by the FDA (Fig. 1): Bortezomib 1 (Velcade, injected cancer therapy),1,2 Crisaborole 2 (Eucrisa, topical eczema treatment),3 Ixazomib 3 (Ninlaro, oral cancer therapy),4–6 Tavaborole 4 (Kerydin, topical anti-fungal),7,8 and Vaborbactam 5.9–11 organoboron compounds display a wide variety of marketable pharmaceutical activities.12,13Our group has a long-standing interest in developing bioactive organoboron compounds,14–34 including boroncontaining capsaicinoids.35,36 Capsaicin (6, Fig. 2) is the colourless, hydrophobic, crystalline compound37 that is responsible for the characteristic spicy “heat” avouring of the chili fruits of the Capsicum genus
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
Summary
Organoboron compounds are beginning to receive wellwarranted attention in the pharmaceutical industry, including ve drugs recently approved by the FDA (Fig. 1): Bortezomib 1 (Velcade, injected cancer therapy), Crisaborole 2 (Eucrisa, topical eczema treatment), Ixazomib 3 (Ninlaro, oral cancer therapy), Tavaborole 4 (Kerydin, topical anti-fungal), and Vaborbactam 5 (in combination with Meropenem as Vabomere, injected broad-spectrum antibiotic). organoboron compounds display a wide variety of marketable pharmaceutical activities.. Organoboron compounds are beginning to receive wellwarranted attention in the pharmaceutical industry, including ve drugs recently approved by the FDA (Fig. 1): Bortezomib 1 (Velcade, injected cancer therapy), Crisaborole 2 (Eucrisa, topical eczema treatment), Ixazomib 3 (Ninlaro, oral cancer therapy), Tavaborole 4 (Kerydin, topical anti-fungal), and Vaborbactam 5 (in combination with Meropenem as Vabomere, injected broad-spectrum antibiotic).. Organoboron compounds display a wide variety of marketable pharmaceutical activities.. Our group has a long-standing interest in developing bioactive organoboron compounds, including boroncontaining capsaicinoids.. Capsaicin (6, Fig. 2) is the colourless, hydrophobic, crystalline compound that is responsible for the characteristic spicy “heat” avouring of the chili fruits of the Capsicum genus. Capsaicinoids are natural products that are structurally related to capsaicin, which tend to display many of the same marketable properties. Include boron-containing capsaicinoids featuring tertiary amides that bear a long aliphatic tail (Fig. 2, 9)
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