Anzurogenin A | 115332-88-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Anzurogenin A
• 英文别名: (25R)-2α,3β,5-trihydroxy-5β-spirostan-6-one；2alpha,3beta,5beta-Trihydroxy-(25r)-spirostan-6-one；(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,15R,16R,18S)-15,16,18-trihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one
• CAS: 115332-88-2
• 化学式: C₂₇H₄₂O₆
• 分子量: 462.627
• InChiKey: XRTVQZVQFIZUBV-ABDXXXKWSA-N

物化性质

• 熔点：
  259-260 °C(Solv: heptane (142-82-5); acetone (67-64-1))
• 沸点：
  596.2±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Anzurogenin A 在 吡啶 作用下， 反应 96.0h， 以143 mg的产率得到anzurogenin A diacetate
  参考文献：
  名称：

  Steroids of the spirostan and furostan series from plants of the genus Allium. Structure of anzurogenin A from Allium suvorovii and A. stipitatum

  摘要：

  DOI：

  10.1007/bf00597575
• 作为产物：
  描述：

  (25R)-spirostan-22α-O-3β,5α,6β-triol 在 吡啶 、 咪唑 、 氢氧化钾 、 高氯酸 、 lithium carbonate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 61.0h， 生成 Anzurogenin A
  参考文献：
  名称：

  Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing

  摘要：

  Eight new 5 beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3 beta-OH, 3 alpha-OH, 2 beta,3 beta-OH, 2 alpha,3 beta-OH, 3 beta-NH2, 2 alpha-NH2-3 beta-OH, 2 beta-NH2-3 beta-OH, and 2 beta-OH-3 beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5 beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3 beta-hydroxy and 2 beta,3 beta-dihydroxy functionality which show promise as environmental friendly insecticides. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.02.024

文献信息

• Novel 5β-hydroxyspirostan-6-ones ecdysteroid antagonists: Synthesis and biological testing
  作者：Daniel G. Rivera、Fredy León、Francisco Coll、Gema P. Davison

  DOI：10.1016/j.steroids.2005.02.024

  日期：2006.1

  Eight new 5 beta-hydroxy-spirostan-6-ones bearing hydroxy and amino functions in the A ring, i.e., 3 beta-OH, 3 alpha-OH, 2 beta,3 beta-OH, 2 alpha,3 beta-OH, 3 beta-NH2, 2 alpha-NH2-3 beta-OH, 2 beta-NH2-3 beta-OH, and 2 beta-OH-3 beta-NH2, were efficiently synthesized, and their antiecdysteroid activities were evaluated on the metamorphosis bioassay of mosquito Aedes aegypti. To our knowledge, these new steroids represent the first 5 beta-hydroxy-spirostanes which have been tested for antiecdysteroid activity in mosquitoes. The higher antagonistic effect was found for compounds bearing the 3 beta-hydroxy and 2 beta,3 beta-dihydroxy functionality which show promise as environmental friendly insecticides. (c) 2005 Elsevier Inc. All rights reserved.
• Steroids of the spirostan and furostan series from plants of the genus Allium. Structure of anzurogenin A from Allium suvorovii and A. stipitatum
  作者：Yu. S. Vollerner、S. D. Kravits、A. S. Shashkov、M. B. Gorovits、N. K. Abubakirov

  DOI：10.1007/bf00597575

  日期：——