5,21-dihydrorhazinilam N-oxide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Rhazinilam生物碱
• 英文名称: 5,21-dihydrorhazinilam N-oxide
• 英文别名: (12R,19R)-12-ethyl-16-oxido-8-aza-16-azoniatetracyclo[10.6.1.02,7.016,19]nonadeca-1(18),2,4,6-tetraen-9-one
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: LYHAEQZONMBWFL-KTVLMBSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,21-dihydrorhazinilam N-oxide 在 氧气 、 iron(II) sulfate 作用下， 生成 rhazinilam
  参考文献：
  名称：

  Hemisynthesis of rhazinilam analogues: structure - activity relationships on tubulin-microtubule system

  摘要：

  Semi-synthesis of derivatives of rhazinilam, an antitubulin compound, delineated some molecular features necessary for biological activity. In the course of this study, the formation of rhazinilam from 1,2-didehydroaspidospermidine is reexamined and a new mechanism is proposed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00391-0
• 作为产物：
  描述：

  eburenine 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到5,21-dihydrorhazinilam N-oxide
  参考文献：
  名称：

  D-ring substituted rhazinilam analogues: semisynthesis and evaluation of antitubulin activity

  摘要：

  Novel (-)- and (+)-rhazinilam derivatives substituted on the D-ring (compounds 3, 4, 5 and 6) have been prepared from (+)-vincadifformine 7 and (-)-tabersonine and evaluated against the disassembly of microtubules into tubulin. Along with this study, a reproducible 'one pot' semisynthesis of (-)-rhazinilam 1 from (+)-1,2-didehydroaspidospermidine 2 was performed allowing the easy preparation of these new compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00241-2

文献信息

• Hemisynthesis of rhazinilam analogues: structure - activity relationships on tubulin-microtubule system
  作者：Bruno David、Thierry Sévenet、Odile Thoison、Khalijah Awang、Mary Païs、Michel Wright、Daniel Guénard

  DOI：10.1016/s0960-894x(97)00391-0

  日期：1997.9

  Semi-synthesis of derivatives of rhazinilam, an antitubulin compound, delineated some molecular features necessary for biological activity. In the course of this study, the formation of rhazinilam from 1,2-didehydroaspidospermidine is reexamined and a new mechanism is proposed. (C) 1997 Elsevier Science Ltd.
• D-ring substituted rhazinilam analogues: semisynthesis and evaluation of antitubulin activity
  作者：Christophe Dupont、Daniel Guénard、Luba Tchertanov、Sylviane Thoret、Françoise Guéritte

  DOI：10.1016/s0968-0896(99)00241-2

  日期：1999.12

  Novel (-)- and (+)-rhazinilam derivatives substituted on the D-ring (compounds 3, 4, 5 and 6) have been prepared from (+)-vincadifformine 7 and (-)-tabersonine and evaluated against the disassembly of microtubules into tubulin. Along with this study, a reproducible 'one pot' semisynthesis of (-)-rhazinilam 1 from (+)-1,2-didehydroaspidospermidine 2 was performed allowing the easy preparation of these new compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.