3-(hydroxymethyl)-2-methyl-3,8a-bis(sulfanyl)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione | 1419872-05-1

• 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: 3-(hydroxymethyl)-2-methyl-3,8a-bis(sulfanyl)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 1419872-05-1
• 化学式: C₉H₁₄N₂O₃S₂
• 分子量: 262.354
• InChiKey: IVUDJWMUQXUKBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  62.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(hydroxymethyl)-2-methyl-3,8a-bis(sulfanyl)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione 在 碘 作用下， 以 乙酸乙酯 为溶剂， 生成 7-(Hydroxymethyl)-11-methyl-8,9-dithia-5,11-diazatricyclo[5.2.2.01,5]undecane-6,10-dione 、 7-(Hydroxymethyl)-12-methyl-8,9,10-trithia-5,12-diazatricyclo[5.3.2.01,5]dodecane-6,11-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
• 作为产物：
  描述：

  N--(S)-serine methylester 在 咪唑 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 硫化氢 、 氢气 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 3-(hydroxymethyl)-2-methyl-3,8a-bis(sulfanyl)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-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.