(E)-3-(2-oxo-2-(pyridin-3-yl)ethylidene)indolin-2-one | 151019-28-2

• 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-(2-oxo-2-(pyridin-3-yl)ethylidene)indolin-2-one
• 英文别名: (3E)-3-(2-oxo-2-pyridin-3-ylethylidene)-1H-indol-2-one
• CAS: 151019-28-2
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: DPVXFHPWUBDVMN-XYOKQWHBSA-N

物化性质

• 沸点：
  503.3±50.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-oxo-2-(pyridin-3-yl)ethylidene)indolin-2-one 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以60%的产率得到3-(2-Oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis of [a]annulated carbazoles from indol-2,3-dione

  摘要：

  Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3-[(2-aryl-2-ethoxycarbonyloxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding [a]annulated carbazoles 10 are obtained via 6pi-electrocyclization.

  DOI：

  10.1016/s0040-4020(01)81301-6
• 作为产物：
  描述：

  3-hydroxy-3-(2-oxo-2-pyridin-3-yl-ethyl)-1,3-dihydro-indol-2-one 在 盐酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (E)-3-(2-oxo-2-(pyridin-3-yl)ethylidene)indolin-2-one
  参考文献：
  名称：

  Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

  摘要：

  通过NMR光谱对3-酰基吲哚类化合物中E/Z几何异构体的命名可能会导致不正确的烯烃立体化学分配，因为在一系列大类类似物中观察到的化学位移范围较窄。相较之下，UV-Vis光谱为烯烃立体化学分配提供了一种方便且更可靠的方法。X射线晶体学与理论研究的结合表明，UV-Vis光谱行为的观察差异与Z-异构体的扭曲构象有关，该构象相对于E-异构体提供了降低的共轭效应和较弱的紫外光移吸收。

  DOI：

  10.1039/c4ob00496e

文献信息

• 1,3-Dipolar cycloaddition reaction of heteroaromatic N-ylides with 3-[(E)-2-aryl(hetaryl)-2-oxoethylidene]indolin-2-ones
  作者：A. B. Serov、V. G. Kartsev、Yu. A. Aleksandrov、F. M. Dolgushin

  DOI：10.1007/s11172-006-0133-2

  日期：2005.10

  A series of 6a′,7′,8′,9′-tetrahydrospiro[indoline-3,7′-pyrrolo[1,2-a]quinoline]-2-one derivatives were synthesized by the 1,3-dipolar cycloaddition reaction. The regio-and stereoselectivity of the reaction were established by X-ray diffraction study.

  通过 1,3-二极环加成反应合成了一系列 6a′,7′,8′,9′-四氢螺[吲哚啉-3,7′-吡咯并[1,2-a]喹啉]-2-酮衍生物。通过 X 射线衍射研究确定了反应的区域和立体选择性。
• Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2
  作者：Cornelius Klöck、Xi Jin、Kihang Choi、Chaitan Khosla、Peter B. Madrid、Andrew Spencer、Brian C. Raimundo、Paul Boardman、Guido Lanza、John H. Griffin

  DOI：10.1016/j.bmcl.2010.12.037

  日期：2011.5

  Inhibitors of human transglutaminase 2 (TG2) are anticipated to be useful in the therapy of a variety of diseases including celiac sprue as well as certain CNS disorders and cancers. A class of 3-acylidene-2-oxoindoles was identified as potent reversible inhibitors of human TG2. Structure-activity relationship analysis of a lead compound led to the generation of several potent, competitive inhibitors. Analogs with significant non-competitive character were also identified, suggesting that the compounds bind at one or more allosteric regulatory sites on this multidomain enzyme. The most active compounds had K(i) values below 1.0 mu M in two different kinetic assays for human TG2, and may therefore be suitable for investigations into the role of TG2 in physiology and disease in animals. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] 3-ACYLIDENE-2-OXOINDOLE DERIVATIVES FOR INHIBITION OF TRANSGLUTAMINASE 2<br/>[FR] DÉRIVÉS 3-ACYLIDÈNE-2-OXOINDOLE DESTINÉS À INHIBER LA TRANSGLUTAMINASE 2
  申请人：NUMERATE INC

  公开号：WO2012078519A2

  公开（公告）日：2012-06-14

  Provided herein are acylidene oxoindole derivatives, compositions including them, and methods of inhibiting transglutaminase 2 and treating diseases mediated by transglutaminase 2 by administering such derivatives and compositions.
• Synthesis of [a]annulated carbazoles from indol-2,3-dione
  作者：Egle M. Beccalli、Alessandro Marchesini、Tullio Pilati

  DOI：10.1016/s0040-4020(01)81301-6

  日期：1993.5

  Reaction of ethyl chloroformate with 3-aroylmethylindol-2(3H)-ones 5 affords the ethyl 3-[(2-aryl-2-ethoxycarbonyloxy)ethenyl]-2-(ethoxycarbonyloxy)indole-1-carboxylates 6 from which the corresponding [a]annulated carbazoles 10 are obtained via 6pi-electrocyclization.
• Studies on the stereochemical assignment of 3-acylidene 2-oxindoles
  作者：Steven J. Edeson、Julong Jiang、Stephen Swanson、Panayiotis A. Procopiou、Harry Adams、Anthony J. H. M. Meijer、Joseph P. A. Harrity

  DOI：10.1039/c4ob00496e

  日期：——

  The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

  通过NMR光谱对3-酰基吲哚类化合物中E/Z几何异构体的命名可能会导致不正确的烯烃立体化学分配，因为在一系列大类类似物中观察到的化学位移范围较窄。相较之下，UV-Vis光谱为烯烃立体化学分配提供了一种方便且更可靠的方法。X射线晶体学与理论研究的结合表明，UV-Vis光谱行为的观察差异与Z-异构体的扭曲构象有关，该构象相对于E-异构体提供了降低的共轭效应和较弱的紫外光移吸收。