trans-3-(3,4,5-trimethoxyphenyl)acrylic acid 3-[4-(3-hydroxypropyl)piperazin-1-yl]propyl ester | 870449-80-2

• 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: trans-3-(3,4,5-trimethoxyphenyl)acrylic acid 3-[4-(3-hydroxypropyl)piperazin-1-yl]propyl ester
• 英文别名: 3-[4-(3-hydroxypropyl)piperazin-1-yl]propyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 870449-80-2
• 化学式: C₂₂H₃₄N₂O₆
• 分子量: 422.522
• InChiKey: KBIXYMGHPRKUKJ-VOTSOKGWSA-N

物化性质

• 沸点：
  584.5±50.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trans-3-(3,4,5-trimethoxyphenyl)acrylic acid 3-[4-(3-hydroxypropyl)piperazin-1-yl]propyl ester 、 9H-芴-9-甲酰氯 以 氯仿 为溶剂， 反应 12.0h， 以60 mg的产率得到9H-Fluorene-9-carboxylic acid 3-(4-{3-[(E)-3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-propyl}-piperazin-1-yl)-propyl ester
  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
• 作为产物：
  描述：

  (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 12.0h， 生成 trans-3-(3,4,5-trimethoxyphenyl)acrylic acid 3-[4-(3-hydroxypropyl)piperazin-1-yl]propyl ester
  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

• 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.