1-methyl-3-hydroxy-3-(2-(4-chlorophenyl)-2-oxoethyl)indolin-2-one | 848-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-hydroxy-3-(2-(4-chlorophenyl)-2-oxoethyl)indolin-2-one
• 英文别名: 1-Methyl-3-hydroxy-2-oxo-3-(4-chlorphenacyl)-indolin；3-[2-(4-chloro-phenyl)-2-oxo-ethyl]-3-hydroxy-1-methyl-1,3-dihydro-indol-2-one；3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxy-1-methyl-1,3-dihydro-2H-indol-2-one；3-[2-(4-chlorophenyl)-2-oxoethyl]-3-hydroxy-1-methylindol-2-one
• CAS: 848-25-9
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: VPZLICFMCPTGJV-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  587.0±50.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-3-hydroxy-3-(2-(4-chlorophenyl)-2-oxoethyl)indolin-2-one 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以76%的产率得到1-methyl-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one
  参考文献：
  名称：

  10.002/cmdc.201402038

  摘要：

  DOI：

  10.002/cmdc.201402038
• 作为产物：
  描述：

  靛红 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-methyl-3-hydroxy-3-(2-(4-chlorophenyl)-2-oxoethyl)indolin-2-one
  参考文献：
  名称：

  10.002/cmdc.201402038

  摘要：

  DOI：

  10.002/cmdc.201402038

文献信息

• 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。
• 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.
• Nogo Receptor Binding Small Molecules to Promote Axonal Growth
  申请人：Strittmatter Stephen M.

  公开号：US20110065715A1

  公开（公告）日：2011-03-17

  The present invention provides a method for identifying compounds which modulate the interaction of Nogo and Nogo receptor (NgR). The present invention also provides compounds that modulate the interaction of Nogo and Nogo receptor (NgR), the use of such compounds and compositions in the treatment or amelioration of conditions diseases or disorders, such as spinal cord injury, traumatic brain injury, stroke, multiple sclerosis, ALS, Huntington's disease, Alzheimer's disease, Parkinson's disease, epilepsy, Schizophrenia or schizoaffective disorders.
• <i>tert</i>‐Butyl Nitrite Promoted Visible‐Light‐Induced Steric‐Hindrance‐Regulated Concurrent Cross‐Coupling and Regioselective Nitration of 3‐Alkylidene‐2‐oxindoles
  作者：Prabhat Sarkar、Soumitra Rana、Debashis Jana、Subham Mandal、Chhanda Mukhopadhyay

  DOI：10.1002/adsc.202301159

  日期：2024.4.9

  A tert‐butyl nitrite (TBN) promoted visible‐light‐induced one‐pot C−N cross coupling reaction of 3‐alkylidene‐2‐oxindoles with benzene‐1,2‐diamine was explored. Simultaneously, the indoline motif of 3‐alkylidene‐2‐oxindoles as well as 3‐ylidene oxindoles are regioselectively nitrated at the C‐6 position by in‐situ formed NO₂ radical. (E)‐3‐(2‐(aryl)‐2‐oxoethylidene)oxindole and (E)‐3‐ylidene oxindole produce distinct nitrated diastereomeric coupling products, a phenomenon influenced by the steric bulk of the functional group. The experimental findings suggest the potential involvement of a radical pathway in this reaction.
• 10.002/cmdc.201402038
  作者：Nagle, Amrita A.、Reddy, Shridhivya A.、Bertrand, Helene、Tajima, Hisashi、Dang, Truong-Minh、Wong, Siew-Cheng、Hayes, John D.、Wells, Geoffrey、Chew, Eng-Hui

  DOI：10.002/cmdc.201402038

  日期：——