Graduate School of Pharmaceutical Sciences and Research Cluster on "Innovative Chemical Sensing", Tokushima University, 1-78-1 Shomachi, Tokushima 770-8505, Japan.
Department of Microbiology and Infection Control Sciences, Kyoto Pharmaceutical University, Misasaginakauchi-cho, Yamashita-Ku, Kyoto 607-8414, Japan.
Mar Drugs. 2020 Jan 30;18(2):92. doi: 10.3390/md18020092.
Side-chain derivatives of eurotiumide A, a dihydroisochroman-type natural product, have been synthesized and their antimicrobial activities described. Sixteen derivatives were synthesized from a key intermediate of the total synthesis of eurotiumide A, and their antimicrobial activities against two Gram-positive bacteria, methicillin-susceptible and methicillin-resistant (MSSA and MRSA), and a Gram-negative bacterium, , were evaluated. The results showed that derivatives having an iodine atom on their aromatic ring instead of the prenyl moiety displayed better antimicrobial activity than eurotiumide A against MSSA and . Moreover, we discovered that a derivative with an isopentyl side chain, which is a hydrogenated product of eurotiumide A, is the strongest antimicrobial agent against all three strains, including MRSA.
已合成了青霉胺 A 的侧链衍生物，这是一种二氢异苯并呋喃型天然产物，并描述了它们的抗菌活性。从青霉胺 A 全合成的关键中间体合成了 16 种衍生物，并评估了它们对两种革兰氏阳性菌（耐甲氧西林金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌）和一种革兰氏阴性菌（铜绿假单胞菌）的抗菌活性。结果表明，与青霉胺 A 相比，具有芳环上碘原子而不是prenyl 部分的衍生物对 MSSA 和 显示出更好的抗菌活性。此外，我们发现一种具有异戊基侧链的衍生物，它是青霉胺 A 的氢化产物，是对包括耐甲氧西林金黄色葡萄球菌在内的所有三种菌株具有最强抗菌活性的物质。
