(3S,5aR,10bR,11aS)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-2-methyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione | 1419872-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S,5aR,10bR,11aS)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-2-methyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
• 英文别名: (1S,3R,11R,14S)-14-[[tert-butyl(dimethyl)silyl]oxymethyl]-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
• CAS: 1419872-01-7
• 化学式: C₂₁H₂₉N₃O₃S₂Si
• 分子量: 463.697
• InChiKey: JWECYLCXHJMUJF-GNBIQWSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 三氟化硼乙醚 、 硫化氢 、 碘 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以27%的产率得到(3S,5aR,10bR,11aS)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-2-methyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
  参考文献：
  名称：

  Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification

  摘要：

  Chaetocin (1), a structurally complex epidithiodiketopiperazine (ETP) alkaloid produced by Chaetomium minutum, is a potent inhibitor of protein lysine methyltransferase G9a, which plays important roles in many biological processes. Here we present our synthetic investigations to identify a simple prototype G9a inhibitor structure based on structure-activity relationship (SAR) studies on chaetocin derivatives. The simple derivative PS-ETP-1 (14) was found to be a potent G9a inhibitor with greatly reduced cytotoxicity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.087

文献信息

• Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification
  作者：Shinya Fujishiro、Kosuke Dodo、Eriko Iwasa、Yuou Teng、Yoshihiro Sohtome、Yoshitaka Hamashima、Akihiro Ito、Minoru Yoshida、Mikiko Sodeoka

  DOI：10.1016/j.bmcl.2012.11.087

  日期：2013.2

  Chaetocin (1), a structurally complex epidithiodiketopiperazine (ETP) alkaloid produced by Chaetomium minutum, is a potent inhibitor of protein lysine methyltransferase G9a, which plays important roles in many biological processes. Here we present our synthetic investigations to identify a simple prototype G9a inhibitor structure based on structure-activity relationship (SAR) studies on chaetocin derivatives. The simple derivative PS-ETP-1 (14) was found to be a potent G9a inhibitor with greatly reduced cytotoxicity. (c) 2012 Elsevier Ltd. All rights reserved.