3-{N-[(2β,15α)-14,15-dihydro-11-oxosecurinan-15-yl]-2-aminoethyl}-1H-indole | 1085244-02-5

• 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: 3-{N-[(2β,15α)-14,15-dihydro-11-oxosecurinan-15-yl]-2-aminoethyl}-1H-indole
• 英文别名: allomargaritarine；(1S,2R,8S,9S)-9-[2-(1H-indol-3-yl)ethylamino]-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadec-11-en-13-one
• CAS: 1085244-02-5
• 化学式: C₂₃H₂₇N₃O₂
• 分子量: 377.486
• InChiKey: IWVPJLXKLFDSTF-QXUYBEEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  色胺 、 一叶秋碱 在 ytterbium(III) triflate 作用下， 以 甲醇 为溶剂， 以80%的产率得到3-{N-[(2β,15α)-14,15-dihydro-11-oxosecurinan-15-yl]-2-aminoethyl}-1H-indole
  参考文献：
  名称：

  叶酸生物碱胺化产物的合成及生物活性

  摘要：

  开发了一种立体有择合成异玛加利特林和其他天然生物碱叶氨酸的胺化产物的方法。通过使用三氟甲磺酸镱作为催化剂，实现了在 securinin 偶氮双环辛烷部分的双键上的胺的立体选择性亲核加成。通过向分子添加药效团引起的安全保护的生物活性显示出实验性的变化。

  DOI：

  10.1007/s10600-008-9013-3

文献信息

• SMALL MOLECULE SECURININE AND NORSECURININE ANALOGS AND THEIR USE IN CANCERS, INFLAMMATORY DISEASES AND INFECTIONS
  申请人：GUNDLURU Mahesha K.

  公开号：US20160229861A1

  公开（公告）日：2016-08-11

  The present invention relates to novel securinine and norsecurine analogs and their applicapility in treating cellular proliferative disorders.
• SMALL MOLECULE SECURININE AND NORSECURININE ANALOGS AND THEIR USE IN INHIBITING MYELOPEROXIDASE
  申请人：GUNDLURU Mahesh K.

  公开号：US20160250196A1

  公开（公告）日：2016-09-01

  The present invention relates to novel securinine and norsecurine analogs that have reduced or non-reduced gamma-delta bond. The present invention also provides for methods of using securinine analogs, comprising administering one or more of the analogs to a myeloperoxidase enzyme, such as an enzyme with or proximal to a cell. As set out herein, the securinine analogs directly bind to and inhibit myeloperoxidase (MPO) activity. Accordingly, contacting or administering the analogs to an MPO enzyme allows for inhibition of MPO activity.
• US9827229B2
  申请人：——

  公开号：US9827229B2

  公开（公告）日：2017-11-28
• Synthesis and biological activity of amination products of the alkaloid securinine
  作者：S. G. Klochkov、S. V. Afanas’eva、V. V. Grigor’ev

  DOI：10.1007/s10600-008-9013-3

  日期：2008.3

  A method for stereospecific synthesis of allomargaritarin and other amination products of the natural alkaloid securinine was developed. Stereoselective nucleophilic addition of an amine at the double bond of the azobicyclooctane moiety of securinin was achieved by using ytterbium triflate as the catalyst. The biological activity of securining caused by adding pharmacophores to the molecule was shown

  开发了一种立体有择合成异玛加利特林和其他天然生物碱叶氨酸的胺化产物的方法。通过使用三氟甲磺酸镱作为催化剂，实现了在 securinin 偶氮双环辛烷部分的双键上的胺的立体选择性亲核加成。通过向分子添加药效团引起的安全保护的生物活性显示出实验性的变化。