2-(2-chloroethoxy)ethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate | 870449-69-7

• 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: 2-(2-chloroethoxy)ethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 870449-69-7
• 化学式: C₁₆H₂₁ClO₆
• 分子量: 344.792
• InChiKey: XPWSVRVBASCIAS-SNAWJCMRSA-N

物化性质

• 沸点：
  475.1±40.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-chloroethoxy)ethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以87%的产率得到2-(2-iodoethoxy)ethyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  设计和合成含有黄酮或色酮部分作为基于P糖蛋白的多药耐药性（MDR）调节剂的氨基酯异二聚体

  摘要：

  在这项研究中，合成了一系列新的异二聚体。这些衍生物是Ñ，ñ -双（链烷醇）胺的芳基的酯或Ñ，ñ -带有甲氧基化的芳基残基与黄酮或色酮部分结合的双（乙氧基乙醇）胺芳基酯。研究了这些新化合物，以评估其对多药耐药性白血病细胞系的P-gp调节活性。一些新化合物显示出良好的MDR逆转活性。有趣的是，该系列新化合物不符合先前合成的带有不同芳族部分的类似物所概述的结构-活性关系（SAR）。对于本文所述的化合物，活性与不同的特征相关，尤其是垫片的特征，这对于与泵的相互作用似乎至关重要。这一事实表明，黄酮或色酮残基的存在会影响这些系列产品的SAR，而且柔性分子可以通过P-gp识别位点找到不同的生产性结合模式。这些结果支持了新化合物的合成，这可能是开发控制P-gp依赖性MDR的药物的有用线索。

  DOI：

  10.1016/j.bmc.2017.11.016
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 氯化亚砜 作用下， 以 氯仿 、 苯 为溶剂， 生成 2-(2-chloroethoxy)ethyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Exploratory Chemistry toward the Identification of a New Class of Multidrug Resistance Reverters Inspired by Pervilleine and Verapamil Models

  摘要：

  On the basis of the present knowledge of the substrate recognition site of ABC transporter proteins and inspired by the structures of verapamil and pervilleine A, a new class of Pgp-mediated multidrug resistance (MDR) reverters has been designed and synthesized. The new compounds are flexible molecules carrying one or two basic nitrogen atoms flanked, at properly modulated distance, by two aromatic moieties. Most of the molecules studied possess MDR inhibitory activity on anthracycline-resistant erythroleukemia K 562 cells, showing a potency that is higher than that of the reference compound verapamil and, in a few cases (7, 12, 13, 17, 20, 22, 28), is in the high nanomolar range. These compounds may be useful leads to develop new MDR reverting agents. In fact, the chemical structure of the class is fairly simple and can be implemented in a variety of ways that will allow the synthesis of new compounds that might be useful leads for the development of drugs to control Pgp-dependent MDR.

  DOI：

  10.1021/jm050542x

文献信息

• Design and synthesis of aminoester heterodimers containing flavone or chromone moieties as modulators of P-glycoprotein-based multidrug resistance (MDR)
  作者：Silvia Dei、Maria Novella Romanelli、Dina Manetti、Niccolò Chiaramonte、Marcella Coronnello、Milena Salerno、Elisabetta Teodori

  DOI：10.1016/j.bmc.2017.11.016

  日期：2018.1

  to be critical for the interaction with the pump. This fact indicates that the presence of a flavone or chromone residue influences the SAR of these series of products, and that flexible molecules can find different productive binding modes with the P-gp recognition site. These results support the synthesis of new compounds that might be useful leads for the development of drugs to control P-gp-dependent

  在这项研究中，合成了一系列新的异二聚体。这些衍生物是Ñ，ñ -双（链烷醇）胺的芳基的酯或Ñ，ñ -带有甲氧基化的芳基残基与黄酮或色酮部分结合的双（乙氧基乙醇）胺芳基酯。研究了这些新化合物，以评估其对多药耐药性白血病细胞系的P-gp调节活性。一些新化合物显示出良好的MDR逆转活性。有趣的是，该系列新化合物不符合先前合成的带有不同芳族部分的类似物所概述的结构-活性关系（SAR）。对于本文所述的化合物，活性与不同的特征相关，尤其是垫片的特征，这对于与泵的相互作用似乎至关重要。这一事实表明，黄酮或色酮残基的存在会影响这些系列产品的SAR，而且柔性分子可以通过P-gp识别位点找到不同的生产性结合模式。这些结果支持了新化合物的合成，这可能是开发控制P-gp依赖性MDR的药物的有用线索。
• Exploratory Chemistry toward the Identification of a New Class of Multidrug Resistance Reverters Inspired by Pervilleine and Verapamil Models
  作者：Elisabetta Teodori、Silvia Dei、Arlette Garnier-Suillerot、Fulvio Gualtieri、Dina Manetti、Cecilia Martelli、Maria Novella Romanelli、Serena Scapecchi、Paiwan Sudwan、Milena Salerno

  DOI：10.1021/jm050542x

  日期：2005.11.1

  On the basis of the present knowledge of the substrate recognition site of ABC transporter proteins and inspired by the structures of verapamil and pervilleine A, a new class of Pgp-mediated multidrug resistance (MDR) reverters has been designed and synthesized. The new compounds are flexible molecules carrying one or two basic nitrogen atoms flanked, at properly modulated distance, by two aromatic moieties. Most of the molecules studied possess MDR inhibitory activity on anthracycline-resistant erythroleukemia K 562 cells, showing a potency that is higher than that of the reference compound verapamil and, in a few cases (7, 12, 13, 17, 20, 22, 28), is in the high nanomolar range. These compounds may be useful leads to develop new MDR reverting agents. In fact, the chemical structure of the class is fairly simple and can be implemented in a variety of ways that will allow the synthesis of new compounds that might be useful leads for the development of drugs to control Pgp-dependent MDR.