Melanson Jennifer A, Landry Maxim F, Lanteigne Martin, McQuillan Katherine, Correa Hebelin, Kerr Russell G, Westcott Stephen A
Department of Chemistry and Biochemistry, Mount Allison University Sackville NB E4L 1G8 Canada
Nautilus Biosciences CRODA Canada Inc., Duffy Research Centre Charlottetown PE C1A 4P3 Canada
RSC Adv. 2021 Jul 23;11(39):24282-24291. doi: 10.1039/d1ra04943g. eCollection 2021 Jul 6.
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.
本研究报道了八种带有长脂肪链的新型含硼辣椒素类化合物的制备，这是我们之前研究的扩展，将叔酰胺衍生物纳入了底物范围。我们的硼部分，即频哪醇硼酸酯（Bpin）片段，已在两个位置引入：作为由藜芦醛还原胺化产生的辣椒素类化合物的芳基取代基，或使用铱催化的硼氢化反应在脂肪族取代基的末端。我们报道，该系列中的大多数化合物表现出中等的抗菌和细胞毒性活性，超过了我们之前研究中所记录的活性。
