Synthesis, bioactivity and structure-activity relationships of new 2-aryl-8-OR-3,4-dihydroisoquinolin-2-iums salts as potential antifungal agents

详细信息    查看全文

• 作者：Li-Fei Zhu^a ; ^&dagger ; ; Zhe Hou^a ; ^&dagger ; ; Kun Zhou^a ; Zong-Bo Tong^b ; Qian Kuang^a ; Hui-Ling Geng^a ; ^{genghuiling5@163.com" class="auth_mail" title="E-mail the corresponding author} ; Le Zhou^a ; ^{zhoulechem@nwsuaf.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Isoquinoline ; 2-Aryl-8-methoxy-3 ; 4-dihydroisoquinolin-2-ium ; Antifungal activity ; Plant pathogenic fungi ; Structure&ndash ; activity relationship
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 May 2016
• 年：2016
• 卷：26
• 期：10
• 页码：2413-2417
• 全文大小：617 K

文摘

As our continuing research on antifungal dihydroisoquinolin-2-ium salts, forty 2-aryl-8-OR-3,4-dihydroisoquinolin-2-ium bromides were synthesized and characterized by spectroscopic analysis. By using the mycelium growth rate method, the compounds were evaluated for antifungal activity against three plant pathogenic fungi and structure–activity relationships (SAR) were derived. The vast majority of the compounds displayed the medium to high activity with inhibition rates of 50–100% at 150 μM. About half of the compounds were more active than their natural model compounds sanguinarine and chelerythrine for all the fungi, and part or most of them were more active than positive drugs thiabendazole and azoxystrobin. SAR analysis showed that both substitution patterns of the C-ring and the type of 8-OR group significantly influenced the activity. Thus, a series of new title compounds with excellent antifungal potency emerged.