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首页> 外文期刊>Acta crystallographica. Section C, Structural chemistry. >Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil
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Synthesis, crystal structures, antiproliferative activities and reverse docking studies of eight novel Schiff bases derived from benzil

机译：苯并衍生八种新型席夫碱的合成，晶体结构，抗增殖活动和逆向对接研究

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摘要

Eight novel Schiff bases derived from benzil dihydrazone ( BDH ) or benzil monohydrazone ( BMH ) and four fused‐ring carbonyl compounds (3‐formylindole, FI ; 3‐acetylindole, AI ; 3‐formyl‐1‐methylindole, MFI ; 1‐formylnaphthalene, FN ) were synthesized and characterized by elemental analysis, ESI–QTOF–MS, 1 H and 13 C NMR spectroscopy, as well as single‐crystal X‐ray diffraction. They are (1 Z ,2 Z )‐1,2‐bis{( E )‐[(1 H ‐indol‐3‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethane ( BDHFI ), C 32 H 24 N 6 , (1 Z ,2 Z )‐1,2‐bis{( E )‐[1‐(1 H ‐indol‐3‐yl)ethylidene]hydrazinylidene}‐1,2‐diphenylethane ( BDHAI ), C 34 H 28 N 6 , (1 Z ,2 Z )‐1,2‐bis{( E )‐[(1‐methyl‐1 H ‐indol‐3‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethane ( BMHMFI ) acetonitrile hemisolvate, C 34 H 28 N 6 ·0.5CH 3 CN, (1 Z ,2 Z )‐1,2‐bis{( E )‐[(naphthalen‐1‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethane ( BDHFN ), C 36 H 26 N 4 , ( Z )‐2‐{( E )‐[(1 H ‐indol‐3‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethanone ( BMHFI ), C 23 H 17 N 3 O, ( Z )‐2‐{( E )‐[1‐(1 H ‐indol‐3‐yl)ethylidene]hydrazinylidene}‐1,2‐diphenylethanone ( BMHAI ), C 24 H 19 N 3 O, ( Z )‐2‐{( E )‐[(1‐methyl‐1 H ‐indol‐3‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethanone ( BMHMFI ), C 24 H 19 N 3 O, and ( Z )‐2‐{( E )‐[(naphthalen‐1‐yl)methylidene]hydrazinylidene}‐1,2‐diphenylethanone ( BMHFN ) C 25 H 18 N 2 O. Moreover, the in vitro cytotoxicity of the eight title compounds was evaluated against two tumour cell lines (A549 human lung cancer and 4T 1 mouse breast cancer) and two normal cell lines (MRC‐5 normal lung cells and NIH 3T3 fibroblasts) by MTT assay. The results indicate that four ( BDHMFI , BDHFN , BMHMFI and BMHFN ) are inactive and the other four ( BDHFI , BDHAI , BMHFI and BMHAI ) show severe toxicities against human A549 and mouse 4T 1 cells, similar to the standard cisplatin. All the compounds exhibited weaker cytotoxicity against normal cells than cancer cells. The Swiss Target Prediction web server was applied for the prediction of protein targets. After analyzing the differences in frequency hits between these active and inactive Schiff bases, 18 probable targets were selected for reverse docking with the Surflex‐dock function in SYBYL‐X 2.0 software. Three target proteins, i.e. human ether‐á‐go‐go‐related (hERG) potassium channel, the inhibitor of apoptosis protein 3 and serine/threonine‐protein kinase PIM1, were chosen as the targets. Finally, the ligand‐based structure–activity relationships were analyzed based on the putative protein target (hERG) docking results, which will be used to design and synthesize novel hERG ion channel inhibitors.
机译：八种新型席夫碱衍生自苯并二浦酮（BDH）或苯齐甲齐氟腙（BMH）和四种熔融环羰基化合物（3-甲酰基吲哚，FI; 3-乙酰吲哚，AI; 3-甲酰基-1-甲基吲哚，MFI; 1-甲酰基萘通过元素分析，ESI-QTOF-MS，1 H和13 C NMR光谱，以及单晶X射线衍射，合成并表征。它们是（1 Z，2 Z）-1,2-BIS {（E） - [（1 H-吲哚-3-基）亚甲基肼]肼肼} -1,2-二苯基乙烷（BDHFI），C 32 H 24 n 6，（1 Z，2 Z）-1,2-BIS {（E） - [1-（1 H-indol-3-Y1）乙基]肼肼} -1,2-二苯基乙烷（Bdhai），C 34 H. 28n 6，（1 z，2 z）-1,2-bis {（e） - [（1-甲基-1 h-indol-3-y1）甲基肼]肼基} -1,2-二苯基乙烷（Bmhmfi）乙腈黄芪，C 34 H 28 N 6·0.5CH 3 CN，（1 Z，2 Z）-1,2-双（e） - [（萘-1-基）亚甲基]肼肼} -1,2-二苯基乙烷（BDHFN），C 36 H 26 N 4，（Z）-2 - {（E） - [（1 H-吲哚-3-基）亚甲基]肼肼} -1,2-二苯基乙烯（BMHFI），C 23 H 17 N 3 O，（Z）-2 - {（e） - [1-（1 H-indol-3-Y1）乙基肼]肼肼} -1,2-二苯基乙酮（BMHAI），C 24 H 19 N 3 O，（Z）-2 - {（e） - [（1-甲基-1 H-indol-3-Y1）甲基肼]肼肼} -1,2-二苯基乙醇（BMHMFI），C 24 H 19 N 3 O， （Z）-2 - {（e） - [（萘-1-基）甲基肼]肼基} -1,2-二苯基乙醇（BMHFN）C 25 H 18 N 2 O.此外，通过MTT测定评估八个标题化合物的体外细胞毒性，对两个肿瘤细胞系（A549人肺癌和4T 1小鼠乳腺癌）和两个正常细胞系（MRC-5正常肺细胞和NIH 3T3成纤维细胞）进行评价。结果表明，四（BDHMFI，BDHFN，BMHMFI和BMHFN）是无活性的，另外四个（BDHFI，Bdhai，BMHFI和BMHI）显示出对人A549和小鼠4T 1细胞的严重毒性，类似于标准的顺铂。所有化合物都表现出比癌细胞对正常细胞的细胞毒性较弱。瑞士目标预测Web服务器应用于蛋白质目标的预测。在分析这些活动和非活动Schiff基地之间的频率命中的差异之后，选择了18个可能的目标，用于在Sybyl-x 2.0软件中使用Surflex-Dock函数反向对接。选择三个靶蛋白，即人醚-A-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-go-geach 3和丝氨酸/苏氨酸 - 蛋白激酶pim1作为靶标。最后，基于推定的蛋白质靶标（HERG）对接结果分析了基于配体的结构 - 活性关系，其将用于设计和合成新的HERG离子通道抑制剂。

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