[(E)-3-(3-methoxyphenyl)prop-2-enoyl] 2,2-dimethylpropanoate | 1026427-36-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [(E)-3-(3-methoxyphenyl)prop-2-enoyl] 2,2-dimethylpropanoate
• CAS: 1026427-36-0
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: DKDWVABORSDQOT-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-2-methylpropionic acid methyl ester 、 [(E)-3-(3-methoxyphenyl)prop-2-enoyl] 2,2-dimethylpropanoate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-(3-(3-methoxyphenyl)-propenoyl-amino)-isobutyric acid methyl ester
  参考文献：
  名称：

  Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone

  摘要：

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.059
• 作为产物：
  描述：

  ethyl (E)-3-(3-methoxyphenyl)acrylate 在 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 4.75h， 生成 [(E)-3-(3-methoxyphenyl)prop-2-enoyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  哌隆定衍生的环磺酰胺（sultams）：合成和体外探索对HeLa癌细胞系的治疗潜力

  摘要：

  设计了带有环磺酰胺（sultam）的新的哌隆金变型，并对其合成进行了描述。我们首次在本文中通过闭环易位方法报道了使用格鲁布斯第二代催化剂（格鲁布斯II）对天然产物衍生的环状磺酰胺的合成和生物学评估。使用维蒂希反应，闭环易位（RCM）和使用混合酸酐合成酰胺的方法，可以中等至良好的产率合成一系列由哌啶子丁衍生的阿马甜。评估所有合成的化合物的抗癌活性，并证明其中一些剂量依赖性地降低了HeLa细胞的生长。在这些7、10和14中，细胞生长明显减少。因此，他们计算出的GI 50 发现该值是0.1或<0.1μM。

  DOI：

  10.1016/j.ejmech.2016.12.022

文献信息

• Piperlongumine (piplartine) and analogues: Antiproliferative microtubule-destabilising agents
  作者：Mary J. Meegan、Seema Nathwani、Brendan Twamley、Daniela M. Zisterer、Niamh M. O'Boyle

  DOI：10.1016/j.ejmech.2016.09.048

  日期：2017.1

  Piperlongumine (piplartine, 1) is a small molecule alkaloid that is receiving intense interest due to its antiproliferative and anticancer activities. We investigated the effects of 1 on tubulin and microtubules. Using both an isolated tubulin assay, and a combination of sedimentation and western blotting, we demonstrated that 1 is a tubulin-destabilising agent. This result was confirmed by immunofluorescence and confocal microscopy, which showed that microtubules in MCF-7 breast cancer cells were depolymerized when treated with 1. We synthesised a number of analogues of 1 to explore structure-activity relationships. Compound 13 had the best cytotoxic profile of this series, showing potent effects in human breast carcinoma MCF-7 cells whilst being relatively non-toxic to non-tumorigenic MCF-10a cells. These compounds will be further developed as potential clinical candidates for the treatment of breast cancer. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines
  作者：Nitin P. Lad、Sarang Kulkarni、Rajiv Sharma、Malcolm Mascarenhas、Mahesh R. Kulkarni、Shivaji S. Pandit

  DOI：10.1016/j.ejmech.2016.12.022

  日期：2017.1

  A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done

  设计了带有环磺酰胺（sultam）的新的哌隆金变型，并对其合成进行了描述。我们首次在本文中通过闭环易位方法报道了使用格鲁布斯第二代催化剂（格鲁布斯II）对天然产物衍生的环状磺酰胺的合成和生物学评估。使用维蒂希反应，闭环易位（RCM）和使用混合酸酐合成酰胺的方法，可以中等至良好的产率合成一系列由哌啶子丁衍生的阿马甜。评估所有合成的化合物的抗癌活性，并证明其中一些剂量依赖性地降低了HeLa细胞的生长。在这些7、10和14中，细胞生长明显减少。因此，他们计算出的GI 50 发现该值是0.1或<0.1μM。
• Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
  作者：Päivi H. Kiviranta、Heikki S. Salo、Jukka Leppänen、Valtteri M. Rinne、Sergiy Kyrylenko、Erkki Kuusisto、Tiina Suuronen、Antero Salminen、Antti Poso、Maija Lahtela-Kakkonen、Erik A.A. Wallén

  DOI：10.1016/j.bmc.2008.07.059

  日期：2008.9

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.