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Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities against succinate-cytochrome c reductase
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2018-03-06 , DOI: 10.1016/j.bmcl.2018.03.014
Hua Cheng , Wei Song , Ren Nie , Yu-Xia Wang , Hui-Lian Li , Xiang-Sheng Jiang , Jun-Jun Wu , Cheng Chen , Qiong-You Wu

Succinate-cytochrome c reductase (SCR) is composed of a mixture of mitochondrial complex II (succinate-ubiquinone oxidoreductase) and complex III (cytochrome bc1 complex). Meanwhile, complexes II and III are two promising targets of numerous antibiotics and fungicides. With an aim to identify new lead structures for SCR, complex II or III, a new series of 4-aryloxy-N-arylanilines were synthesized by introducing a 4-aryloxy phenyl group as one of the aryl groups in diaryl amines. With the economic Cu(OAc)2·H2O as the optimal copper promoter, a simple and facile protocol was utilized to afford 24 target products in 56–93% yields. Furthermore, extensive screening results suggested variable inhibitory activities of these compounds against SCR. Exceptionally, compounds 7k7n showed excellent inhibition potency with their IC50 values in the nanomolar range, demonstrating higher potency than the commercial controls (penthiopyrad and azoxystrobin) by over one order of magnitude.



中文翻译:

新的4-芳氧基-N-苯胺的合成及其对琥珀酸-细胞色素c还原酶的抑制活性

琥珀酸-细胞色素c还原酶(SCR)由线粒体复合物II(琥珀酸-泛醌氧化还原酶)和复合物III(细胞色素bc 1复合物)的混合物组成。同时,复合物II和III是众多抗生素和杀真菌剂的两个有希望的靶标。为了鉴定用于SCR,络合物II或III的新的铅结构,通过引入4-芳氧基苯基作为二芳基胺中的芳基之一,合成了一系列新的4-芳氧基-N-芳基苯胺。具有经济性的Cu(OAc)2 ·H 2作为一种最佳的铜促进剂,O被用作一种简单易行的方案,以56-93%的产率提供了24种目标产物。此外,广泛的筛选结果表明这些化合物对SCR的抑制活性不同。例外地,化合物7k - 7n在纳摩尔范围内的IC 50值显示出优异的抑制效能,比商用对照品(苯硫吡喃和嘧菌酯)的效能高出一个数量级。

更新日期:2018-03-06
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