3-hydroxy-3-(2-(4-methoxyphenyl)-2-oxoethyl)-1-methylindolin-2-one | 851-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-3-(2-(4-methoxyphenyl)-2-oxoethyl)-1-methylindolin-2-one
• 英文别名: PT-2-64；1-Methyl-3-hydroxy-2-oxo-3-(4-methoxy-phenacyl)-indolin；1-methyl-3-hydroxy-3-(2-oxo-2-(4-methoxyphenyl)ethyl)-indolin-2-one；3-hydroxy-3-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-1-methyl-1,3-dihydro-indol-2-one；3-hydroxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]-1-methyl-1,3-dihydro-2H-indol-2-one；3-hydroxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]-1-methylindol-2-one
• CAS: 851-02-5
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: BAXBKBGJFIJIIT-UHFFFAOYSA-N

物化性质

• 沸点：
  597.3±50.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(2-(4-methoxyphenyl)-2-oxoethyl)-1-methylindolin-2-one 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-Methyl-3-<4-methoxy-phenacyliden>-oxindol
  参考文献：
  名称：

  Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds

  摘要：

  开发了一种高效的立体选择性反式环丙烷化反应，用于合成3-烷基亚基氧化吲哚与现场生成的α-重氮羰基化合物或α,β-不饱和重氮化合物的反应，无需金属条件即可合成3-螺环丙基-2-氧化吲哚衍生物。该方法基于相应重氮化合物在碱催化条件下的1,3-偶极特性。该方法具有广泛的底物范围，并使用易于获得的起始材料。

  DOI：

  10.1055/a-1384-1967
• 作为产物：
  描述：

  2-吲哚酮 在 四丁基氟化铵 、 sodium hydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.0h， 生成 3-hydroxy-3-(2-(4-methoxyphenyl)-2-oxoethyl)-1-methylindolin-2-one
  参考文献：
  名称：

  2-氧辛酮与酮的自氧化/羟醛串联反应：3-羟基-2-氧辛酮合成的绿色方法

  摘要：

  在DMF中存在四丁基氟化铵和分子筛（MS）4Å的情况下，已开发出室温下空气中2-氧吲哚与酮的有效自氧化反应。这种方法可能为多种生物学上重要的3-羟基-3-（2-氧代烷基）-2-氧吲哚提供绿色，实用且不含金属的方案。

  DOI：

  10.1002/chem.201504282

文献信息

• [EN] METHODS AND COMPOSITIONS FOR TREATING EWINGS SARCOMA FAMILY OF TUMORS<br/>[FR] MÉTHODES ET COMPOSITIONS PERMETTANT DE TRAITER DES TUMEURS DE LA FAMILLE DU SARCOME D'EWING
  申请人：UNIV GEORGETOWN

  公开号：WO2013155341A1

  公开（公告）日：2013-10-17

  Compounds, compositions and methods relating to EWS-FLIl protein inhibitors are provided. The compounds have utility in the treatment of cancers including the Ewing's sarcoma family of tumors.

  提供与EWS-FLIl蛋白抑制剂相关的化合物、组合物和方法。这些化合物在治疗包括Ewing肉瘤家族在内的癌症中具有用途。
• Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive
  作者：Wen-Bing Chen、Yu-Hua Liao、Xi-Lin Du、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1039/b906684e

  日期：——

  In the presence of molecular sieve (MS) 4 Å in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-substituted-3-hydroxyindolin-2-ones in good to excellent yields.

  在DMF中存在4 Å分子筛（MS）的情况下，已经开发出一种无需催化剂的醛酮缩合反应，可以在温和条件下使多种芳香和脂肪酮与靛红反应。这种方法可能提供了一条途径，以良好至优异的产率合成广泛的3-取代-3-羟基吲哚-2-酮。
• 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。
• Proline-Catalyzed Diastereoselective Synthesis of Dihydroquinolinyl-Spirooxindole via Aza-Michael/Aldol Reaction
  作者：Raju Adepu、Prathama S. Mainkar、Damodar Enagandhula

  DOI：10.1055/a-2116-5517

  日期：2023.10

  An efficient diastereoselective synthesis of 1′,4′-dihydro-2′H-spiro[indoline-3,3′-quinolin]-2-one derivatives was achieved using catalytic amount of l-proline. The key reactions involved in the present tandem reaction are aza-Michael addition and aldol reaction. This atom economic reaction proceeded under mild conditions with a broad substrate scope and excellent diastereoselectivity in good to excellent

  利用催化量的我-脯氨酸。目前串联反应中涉及的关键反应是氮杂迈克尔加成和羟醛反应。该原子经济反应在温和的条件下进行，具有广泛的底物范围和优异的非对映选择性，产率良好至优异。
• Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
  作者：Chada Narsimha Reddy、V. Lakshma Nayak、Geeta Sai Mani、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Ram Awatar Maurya、Ahmed Kamal

  DOI：10.1016/j.bmcl.2015.08.056

  日期：2015.10

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.