methyl 3-((4-(allylthio)-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)propanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-((4-(allylthio)-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)propanoate
• 英文别名: Methyl 3-[(3,6-dioxo-4-prop-2-enylsulfanylcyclohexa-1,4-dien-1-yl)amino]propanoate；methyl 3-[(3,6-dioxo-4-prop-2-enylsulfanylcyclohexa-1,4-dien-1-yl)amino]propanoate
• 化学式: C₁₃H₁₅NO₄S
• 分子量: 281.332
• InChiKey: UXIUQFUAFHBZAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  S-allylisothiouronium bromide 、 3-氨基丙酸甲酯 、 对苯二酚 在 sodium iodide 、 sodium chloride 作用下， 以 水 、 乙腈 为溶剂， 以61%的产率得到methyl 3-((4-(allylthio)-3,6-dioxocyclohexa-1,4-dien-1-yl)amino)propanoate
  参考文献：
  名称：

  Discovery and optimization of 2-thio-5-amino substituted benzoquinones as potent anticancer agents

  摘要：

  Based on our discovered novel lead compound 1 through phenotypic drug discovery (PDD) approaches, systematic structural optimization was performed. A series of 2-allylthio-5-amino substituted benzoquinones were synthesized and evaluated for their in-vitro anticancer activities against human prostate cancer cell line PC3. The compound 7a was found inhibit the growth of PC3 with an IC50 of 0.22 mu M, which is over 20-fold improvement compared to lead compound 1. It is noteworthy that compound 7a also showed potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cell, as well as good water solubility. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.059

文献信息

• Discovery and optimization of 2-thio-5-amino substituted benzoquinones as potent anticancer agents
  作者：Yuqiong Zhao、Yihuan Lu、Ridong Li、Jianan He、Han Zhang、Xin Wang、Zemei Ge、Runtao Li

  DOI：10.1016/j.ejmech.2018.02.059

  日期：2018.4

  Based on our discovered novel lead compound 1 through phenotypic drug discovery (PDD) approaches, systematic structural optimization was performed. A series of 2-allylthio-5-amino substituted benzoquinones were synthesized and evaluated for their in-vitro anticancer activities against human prostate cancer cell line PC3. The compound 7a was found inhibit the growth of PC3 with an IC50 of 0.22 mu M, which is over 20-fold improvement compared to lead compound 1. It is noteworthy that compound 7a also showed potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cell, as well as good water solubility. (C) 2018 Elsevier Masson SAS. All rights reserved.