(7S,10S,E)-7-isopropyl-4,4-dimethyl-10-(4-(tritylthio)but-1-enyl)-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadec-1(17)-ene-2,5,8,12-tetraone | 1315334-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (7S,10S,E)-7-isopropyl-4,4-dimethyl-10-(4-(tritylthio)but-1-enyl)-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadec-1(17)-ene-2,5,8,12-tetraone
• CAS: 1315334-39-4
• 化学式: C₄₀H₄₄N₄O₅S₂
• 分子量: 724.945
• InChiKey: IRUUUMPGCCGQNX-PNJLSWBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126.49
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (7S,10S,E)-7-isopropyl-4,4-dimethyl-10-(4-(tritylthio)but-1-enyl)-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadec-1(17)-ene-2,5,8,12-tetraone 在 三乙基硅烷 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以12%的产率得到(7S,10S)-7-isopropyl-10-((E)-4-mercaptobut-1-en-1-yl)-4,4-dimethyl-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadeca-1(17),15(18)-diene-2,5,8,12-tetraone
  参考文献：
  名称：

  Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability

  摘要：

  The total synthesis of largazole and four analogues is reported. All analogues were nanomolar HDAC inhibitors. The antiproliferative activity is driven by lipophilicity and cell permeability. In murine liver homogenates, largazole is rapidly metabolized (half-life <= 5 min) to the thiol which has a half-life of 51 min. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.024
• 作为产物：
  描述：

  在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以108 mg的产率得到(7S,10S,E)-7-isopropyl-4,4-dimethyl-10-(4-(tritylthio)but-1-enyl)-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadec-1(17)-ene-2,5,8,12-tetraone
  参考文献：
  名称：

  Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability

  摘要：

  The total synthesis of largazole and four analogues is reported. All analogues were nanomolar HDAC inhibitors. The antiproliferative activity is driven by lipophilicity and cell permeability. In murine liver homogenates, largazole is rapidly metabolized (half-life <= 5 min) to the thiol which has a half-life of 51 min. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.024