(6E,8S,11S,12E)-11-amino-8-propan-2-yl-1-oxa-4,9-diazacyclotrideca-6,12-diene-5,10-dione | 1309924-33-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (6E,8S,11S,12E)-11-amino-8-propan-2-yl-1-oxa-4,9-diazacyclotrideca-6,12-diene-5,10-dione
• CAS: 1309924-33-1
• 化学式: C₁₃H₂₁N₃O₃
• 分子量: 267.328
• InChiKey: YVGKAIRVEVFWLG-IIKFNFNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6E,8S,11S,12E)-11-amino-8-propan-2-yl-1-oxa-4,9-diazacyclotrideca-6,12-diene-5,10-dione 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 (S)-2-(3-dodecylureido)-N-((6E,8S,11S,12E)-8-isopropyl-5,10-dioxo-1-oxa-4,9-diazacyclotrideca-6-12-dien-11-yl)-3-methylbutanamide
  参考文献：
  名称：

  Syntheses and cytotoxicity of syringolin B-based proteasome inhibitors

  摘要：

  The concise and modular total synthesis of the bacterial natural product and irreversible proteasome inhibitor syringolin B has been achieved. This synthesis has enabled the ready preparation of three diverse, structurally modified syringolin derivatives. The actions of these compounds in inhibiting the proliferation of neuroblastoma cell lines was evaluated, and significant enhancements in potency compared to the natural product were realized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.048
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl ((S,E)-4-(2-(2-(diethoxyphosphoryl)acetamido)ethoxy)-1-(((S)-1-hydroxy-3-methylbutan-2-yl)amino)-1-oxobut-3-en-2-yl)carbamate 在 哌啶 、 四甲基乙二胺 、 zinc trifluoromethanesulfonate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (6E,8S,11S,12E)-11-amino-8-propan-2-yl-1-oxa-4,9-diazacyclotrideca-6,12-diene-5,10-dione
  参考文献：
  名称：

  Syntheses and cytotoxicity of syringolin B-based proteasome inhibitors

  摘要：

  The concise and modular total synthesis of the bacterial natural product and irreversible proteasome inhibitor syringolin B has been achieved. This synthesis has enabled the ready preparation of three diverse, structurally modified syringolin derivatives. The actions of these compounds in inhibiting the proliferation of neuroblastoma cell lines was evaluated, and significant enhancements in potency compared to the natural product were realized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.048

文献信息

• SYNTHESIS OF SYRBACTIN PROTEASOME INHIBITORS
  申请人：The Regents of the University of California

  公开号：EP2507219B1

  公开（公告）日：2018-05-09
• NOVEL SYRINGOLIN ANALOGUES AND METHODS OF MAKING AND USING SAME
  申请人：BROWN UNIVERSITY

  公开号：US20200216401A1

  公开（公告）日：2020-07-09

  The present invention provides, in certain aspects, novel syringolin analogues, In certain embodiments, the compounds of the invention are proteasome inhibitors, In other embodiments, the compounds treat or prevent a cancer such as, but not limited to, leukemia in a subject,
• US9221772B2
  申请人：——

  公开号：US9221772B2

  公开（公告）日：2015-12-29
• US9359309B2
  申请人：——

  公开号：US9359309B2

  公开（公告）日：2016-06-07
• US9783572B2
  申请人：——

  公开号：US9783572B2

  公开（公告）日：2017-10-10