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Synthesis, bioactivity and structure–activity relationships of new 2-aryl-8-OR-3,4-dihydroisoquinolin-2-iums salts as potential antifungal agents
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2016-04-01 , DOI: 10.1016/j.bmcl.2016.04.001
Li-Fei Zhu , Zhe Hou , Kun Zhou , Zong-Bo Tong , Qian Kuang , Hui-Ling Geng , Le Zhou

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.



中文翻译:

新型2-芳基-8-OR-3,4-二氢异喹啉-2-盐作为潜在抗真菌剂的合成,生物活性和构效关系

随着我们对抗真菌二氢异喹啉-2-鎓盐的不断研究,合成了四十个2-芳基-8-OR-3,4-二氢异喹啉-2-鎓溴化物,并通过光谱分析对其进行了表征。通过使用菌丝体生长速率方法,评估了这些化合物对三种植物病原真菌的抗真菌活性,并推导出了结构-活性关系(SAR)。绝大多数化合物在150μM时显示中等至高活性,抑制率为50–100%。在所有真菌中,大约一半的化合物比其天然模型化合物血红素和白屈菜红碱具有更高的活性,并且它们的一部分或大部分都比阳性药物噻苯达唑和嘧菌酯具有更高的活性。SAR分析表明,C环的取代方式和8-OR基团的类型均显着影响活性。因此,

更新日期:2016-04-01
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