(E)-3-(pyridin-2-ylmethylene)indolin-2-one | 141946-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-3-(pyridin-2-ylmethylene)indolin-2-one
• 英文别名: (3E)-3-(2-pyridylmethylene)indolin-2-one；(3E)-3-(pyridin-2-ylmethylidene)-1H-indol-2-one
• CAS: 141946-34-1
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: YKQONSWBHGBDSB-FMIVXFBMSA-N

物化性质

• 熔点：
  202-203 °C(Solv: ethanol (64-17-5))
• 沸点：
  457.2±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(pyridin-2-ylmethylene)indolin-2-one 在 copper(l) iodide 、 potassium carbonate 作用下， 以 水 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 54.0h， 生成 (E)-2-(acetoxymethyl)-6-(4-((2-oxo-3-(pyridin-2-ylmethylene)indolin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  三唑连接的吲哚和吲哚酮糖缀合物作为潜在抗癌剂的调查：新颖的Akt / PKB信号通路抑制剂†往最‡

  摘要：

  为了继续进行新型生物活性剂的合成，我们从吲哚/羟吲哚（29种化合物）合成了两组三唑连接的糖缀合物，并通过IR（红外光谱），1 H NMR（核磁共振）进行了进一步表征，13 C NMR和质谱分析。评估了新合成的目标化合物对DU145（前列腺癌），HeLa（宫颈癌），A549（肺癌）和MCF-7（乳腺癌）细胞系的初步体外抗癌活性。在磺基罗丹明B（SRB）分析中，结果表明化合物5f（吲哚衍生物）和E -9b（羟吲哚衍生物）对DU145细胞显示出显着的细胞毒活性。此外，集落形成测定法（软琼脂测定法）表明化合物5f和E -9b可以抑制DU145细胞的生长和增殖。在DU145细胞中评估了活性最高的细胞毒性化合物5f和E -9b对细胞周期分布的影响，该细胞在亚G1期表现出细胞周期停滞。接下来，化合物5f和E -9b对DU145细胞中的半胱天冬酶激活进行了测试，结果表明这些化合物具有通过内在途径诱导细胞凋

  DOI：

  10.1039/c5md00513b
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-吲哚酮 在 哌啶 作用下， 以 甲醇 为溶剂， 以64.4%的产率得到(E)-3-(pyridin-2-ylmethylene)indolin-2-one
  参考文献：
  名称：

  Discovery of hybrids of indolin-2-one and nitroimidazole as potent inhibitors against drug-resistant bacteria

  摘要：

  随着抗生素耐药性迅速发展，需要发现新的抗菌剂。我们合成了11种吲哚啉-2-酮化合物，并发现一种吲哚啉-2-酮和硝基咪唑的杂合物3-((1-甲基-5-硝基-1H-咪唑-2-基)亚甲基)吲哚啉-2-酮对金黄色葡萄球菌菌株效果显著。为了提高其疗效，我们进一步设计和合成了该化合物的六种衍生物。在经过第二轮结构优化后，一种新型的吲哚啉-2-酮与硝基咪唑的杂合物3-((1-甲基-5-硝基-1H-咪唑-2-基)亚甲基)-5-硝基吲哚啉-2-酮在吲哚啉-2-酮的C-5位置上带有一个硝基，显示出对MRSA ATCC 33591显著的抗菌活性，表明MIC值较低。此外，该分子在革兰氏阴性菌和耐万古霉素菌株中也表现出活性。时间杀菌曲线实验显示其良好的杀菌活性。低溶血率表明其具有良好的安全性。

  DOI：

  10.1038/s41429-018-0076-5

文献信息

• Discovery of hybrids of indolin-2-one and nitroimidazole as potent inhibitors against drug-resistant bacteria
  作者：Yuanzheng Zhou、Yuan Ju、Yang Yang、Zitai Sang、Zhenling Wang、Gu He、Tao Yang、Youfu Luo

  DOI：10.1038/s41429-018-0076-5

  日期：2018.10

  With antibiotics resistance developing rapidly, new antibacterial agents are needed to be discovered. We readily synthesized 11 indolin-2-one compounds and found a hybrid of indolin-2-one and nitroimidazole 3-((1-methyl-5-nitro-1H-imidazol-2-yl)methylene)indolin-2-one to be effective on Staphylococcus aureus strains. Six derivatives of this compound were further designed and synthesized in order to enhance its efficacy. After a second turn of structural refinement, a novel hybrid of indolin-2-one and nitroimidazole 3-((1-methyl-5-nitro-1H-imidazol-2-yl)methylene)-5-nitroindolin-2-one with a nitro group on C-5 position of indolin-2-one was shown to exhibit remarkable antibacterial activities with a low MIC value against MRSA ATCC 33591. Besides, this molecule demonstrated its potency on Gram-negative bacteria and VRE strain. The time-killing curve experiment showed its good bactericidal activity. Low hemolytic rate suggested its promising safety profile.

  随着抗生素耐药性迅速发展，需要发现新的抗菌剂。我们合成了11种吲哚啉-2-酮化合物，并发现一种吲哚啉-2-酮和硝基咪唑的杂合物3-((1-甲基-5-硝基-1H-咪唑-2-基)亚甲基)吲哚啉-2-酮对金黄色葡萄球菌菌株效果显著。为了提高其疗效，我们进一步设计和合成了该化合物的六种衍生物。在经过第二轮结构优化后，一种新型的吲哚啉-2-酮与硝基咪唑的杂合物3-((1-甲基-5-硝基-1H-咪唑-2-基)亚甲基)-5-硝基吲哚啉-2-酮在吲哚啉-2-酮的C-5位置上带有一个硝基，显示出对MRSA ATCC 33591显著的抗菌活性，表明MIC值较低。此外，该分子在革兰氏阴性菌和耐万古霉素菌株中也表现出活性。时间杀菌曲线实验显示其良好的杀菌活性。低溶血率表明其具有良好的安全性。
• Syntheses of spiro[cyclopropane-1,3′-oxindole]-2-carboxylic acid and cyclopropa[c]quinoline-7b-carboxylic acid and their derivatives
  作者：Sarah R. Yong、Alison T. Ung、Stephen G. Pyne、Brian W. Skelton、Allan H. White

  DOI：10.1016/j.tet.2006.11.051

  日期：2007.1

  The synthesis of spiro[cyclopropane-1,3′-oxindole]-2-carboxylic acid, including novel 3-(2- and 3-pyridyl)-substituted analogues and the novel cyclopropa[c]quinoline-7b-carboxylic acid and their ester and amide derivatives is described. These syntheses involve diastereoselective cyclopropanation reactions of methyl 2-(2-nitrophenyl)acrylate and (3E)-(pyridin-2-ylmethylene)- and (3E)-(pyridin-3-ylmethylene)-1

  螺环[环丙烷-1,3'-羟吲哚] -2-羧酸的合成，包括新型的3-（2-和3-吡啶基）取代的类似物以及新型的环丙烷[ c ]喹啉-7b-羧酸及其衍生物描述了酯和酰胺衍生物。这些合成涉及2-（2-硝基苯基）丙烯酸甲酯与（3E）-（吡啶-2-基亚甲基）-和（3E）-（吡啶-3-基亚甲基）-1,3-二氢- 2 H-吲哚-2-酮与乙酸乙酯（二甲基亚硫烷基）乙酸酯（EDSA）。甲基环丙烷的合成[ c]喹啉-7b-羧酸盐涉及硝基二酯前体的区域选择性还原环化。关键化合物的相对立体化学已通过单晶X射线结构分析确定。
• CURCUMIN ANALOGS WITH ANTI-TUMOR AND ANTI-ANGIOGENIC PROPERTIES
  申请人：Snyder James P.

  公开号：US20080234320A1

  公开（公告）日：2008-09-25

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及展现抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的制药配方和使用这些化合物的方法。
• Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity
  作者：Wei Zhang、Mei-Lin Go

  DOI：10.1016/j.bmc.2008.12.052

  日期：2009.3

  Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventive potential. To investigate this possibility, we have synthesized and evaluated a series of functionalized 3-benzylidene-indolin-2-ones for induction of NQO1 in murine Hepa1c1c7 cells as well as antiproliferative activity against two human cancer cell lines (MCF-7, HCT116). The benzylideneindolinones were found to be good inducers of NQO1 activity, with 85% of test compounds able to increase basal NQO1 activity by more than twofold at concentrations of <= 10 mu M. By contrast, fewer compounds (11%) tested at the same concentration were able to reduce cell viability by more than 50%. Structure activity relationships showed that the nitrogen linked Michael acceptor moiety was an essential requirement for both activities. This common feature notwithstanding, substitution of the 3-benzylidene-indolin-2-one core structure affected NQO1 induction and antiproliferative activities in dissimilar ways, underscoring different structural requirements for these two activities. Nonetheless, promising compounds ( 10, 42, 45-48) were identified that combine selective induction of NQO1 with potent antiproliferative activity. A potential advantage of such agents would be the ability to provide added protection to normal cells by the up-regulation of NQO1 and other phase II enzymes while simultaneously targeting neoplastic cells. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and cardiotonic activity of pyridylmethylene-2-indolinones
  作者：A Andreani、M Rambaldi、A Locatelli、A Bongini、R Bossa、I Galatulas、M Ninci

  DOI：10.1016/0223-5234(92)90106-b

  日期：1992.3

  The title compounds were prepared by reaction of 3 2-indolinones with 3 different pyridinecarboxaldehydes. In one case (7b) it was possible to isolate and characterize both the E and Z isomers. In the other cases (except 5b) the E isomer was largely predominant or the only one present. The pharmacological activity of E-7b was not significantly different from that of Z-7b. Compound 6b, arising from the reaction of 5-methoxy-2-indolinone with 3-pyridinecarboxaldehyde, was significantly more active than the other compounds prepared.