(E)-1-(1-methyl-1H-indol-2-yl)ethanone oxime | 54279-25-3

• 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)-1-(1-methyl-1H-indol-2-yl)ethanone oxime
• 英文别名: (E)-1-(1-methylindol-2-yl)ethanone oxime；(NE)-N-[1-(1-methylindol-2-yl)ethylidene]hydroxylamine
• CAS: 54279-25-3
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: ZLCSVDRCURJFQR-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(1-methyl-1H-indol-2-yl)ethanone oxime 在 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 (E,E)-2-(2-((1-(1-methylindol-2-yl)ethylidene)aminooxymethyl)phenyl)-2-methoxyimino-N-methylacetamide
  参考文献：
  名称：

  新型吲哚类杀菌剂吲哚类肟肟星闪霉素衍生物的设计，合成及生物活性

  摘要：

  设计并合成了二十一种含有吲哚部分的新型肟醚类球果素，它们利用吲哚基稳定了依诺斯特罗宾中的E-苯乙烯基。生物学测定表明大多数化合物表现出有效的杀真菌活性。结构-活性关系研究表明，合成的3-甲氧基丙酸甲酯肟醚7b-e在所有合成的肟醚化合物7中均表现出很高的活性。此外，α-（甲氧基亚氨基）苯乙酸甲酯肟醚化合物7f-i和N-甲氧基-氨基甲酸甲酯化合物7j-m的杀真菌活性 与氨解反应的相应产物相比，显示出显着差异。

  DOI：

  10.1111/cbdd.12460
• 作为产物：
  描述：

  1-(1-甲基-1H-吲哚-2-基)乙酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以98.3%的产率得到(E)-1-(1-methyl-1H-indol-2-yl)ethanone oxime
  参考文献：
  名称：

  新型吲哚类杀菌剂吲哚类肟肟星闪霉素衍生物的设计，合成及生物活性

  摘要：

  设计并合成了二十一种含有吲哚部分的新型肟醚类球果素，它们利用吲哚基稳定了依诺斯特罗宾中的E-苯乙烯基。生物学测定表明大多数化合物表现出有效的杀真菌活性。结构-活性关系研究表明，合成的3-甲氧基丙酸甲酯肟醚7b-e在所有合成的肟醚化合物7中均表现出很高的活性。此外，α-（甲氧基亚氨基）苯乙酸甲酯肟醚化合物7f-i和N-甲氧基-氨基甲酸甲酯化合物7j-m的杀真菌活性 与氨解反应的相应产物相比，显示出显着差异。

  DOI：

  10.1111/cbdd.12460

文献信息

• Optimization and structure–activity relationships of a series of potent inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase as novel antimicrobial agents
  作者：Nag S. Kumar、Emily A. Amandoron、Artem Cherkasov、B. Brett Finlay、Huansheng Gong、Linda Jackson、Sukhbir Kaur、Tian Lian、Anne Moreau、Christophe Labrière、Neil E. Reiner、Raymond H. See、Natalie C. Strynadka、Lisa Thorson、Edwin W.Y. Wong、Liam Worrall、Roya Zoraghi、Robert N. Young

  DOI：10.1016/j.bmc.2012.10.002

  日期：2012.12

  A novel series of hydrazones were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as one of the most highly connected 'hub proteins' in MRSA. PK has been shown to be critical for bacterial survival which makes it a potential target for development of novel antibiotics and the high degree of connectivity implies it should be very sensitive to mutations and thus less able to develop resistance. PK is not unique to bacteria and thus a critical requirement for such a PK inhibitor would be that it does not inhibit the homologous human enzyme(s) at therapeutic concentrations. Several MRSA PK inhibitors (including 8d) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to four human PK isoforms (M1, M2, R and L). However these lead compounds did not show significant inhibitory activity for MRSA growth presumably due to poor bacterial cell penetration. Structure-activity relationship (SAR) studies were carried out on 8d and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. These inhibitors bind in two elongated flat clefts found at the minor interfaces in the homo-tetrameric enzyme complex and the observed SAR is in keeping with the size and electronic constraints of these binding sites. Access to the corresponding sites in the human enzyme is blocked. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Biological Activity of Oxime Ether Strobilurin Derivatives Containing Indole Moiety as Novel Fungicide
  作者：Ya-Qiang Xie、Zi-Long Huang、Hui-Dong Yan、Jun Li、Li-Yi Ye、Li-Ming Che、Song Tu

  DOI：10.1111/cbdd.12460

  日期：2015.6

  Twenty‐one novel oxime ether strobilurins containing indole moiety, which employed an indole group to stabilize the E‐styryl group in Enoxastrobin, were designed and synthesized. The biological assay indicated that most compounds exhibited potent fungicidal activities. The structure–activity relationship study demonstrated that the synthesized methyl 3‐methoxypropenoate oxime ethers 7b–e exhibited remarkably

  设计并合成了二十一种含有吲哚部分的新型肟醚类球果素，它们利用吲哚基稳定了依诺斯特罗宾中的E-苯乙烯基。生物学测定表明大多数化合物表现出有效的杀真菌活性。结构-活性关系研究表明，合成的3-甲氧基丙酸甲酯肟醚7b-e在所有合成的肟醚化合物7中均表现出很高的活性。此外，α-（甲氧基亚氨基）苯乙酸甲酯肟醚化合物7f-i和N-甲氧基-氨基甲酸甲酯化合物7j-m的杀真菌活性 与氨解反应的相应产物相比，显示出显着差异。