5α-22-isoallospirost-9(11)-en-3β-ol 3-acetate | 914-85-2

• 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: 5α-22-isoallospirost-9(11)-en-3β-ol 3-acetate
• 英文别名: (25R)-3β-acetoxy-5α-spirost-9(11)-ene；(25R)-3β-Acetoxy-5α-spirost-9(11)-en；(25R)-3β-Acetoxy-5α-spirost-9(11)-en, 9-Dehydro-tigogeninacetat；[(1S,2S,4S,5'R,6R,7S,8R,9S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-11-ene-6,2'-oxane]-16-yl] acetate
• CAS: 914-85-2
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: MQMIKMFVYXKKQY-ANAKBLJVSA-N

物化性质

• 熔点：
  193-198 °C
• 沸点：
  535.8±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5α-22-isoallospirost-9(11)-en-3β-ol 3-acetate 在 四氢呋喃 、 sodium hydroxide 作用下， 生成 (3β,5Alpha,25R)3-羟基螺甾-9(11)-烯
  参考文献：
  名称：

  The Conversion of Hecogenin to ▵^7,9(11)-22-isoallospirostadiene-3β-ol¹

  摘要：

  DOI：

  10.1021/ja01109a061
• 作为产物：
  描述：

  (25R)-3β-Acetoxy-5α-spirostan-11α-ol 在 吡啶 、 2,4,6-三甲基吡啶 作用下， 生成 5α-22-isoallospirost-9(11)-en-3β-ol 3-acetate
  参考文献：
  名称：

  Steroids. LIII.¹ Steroidal Sapogenins. XXXII.² The Dehydration of 11α-Hydroxy Steroids

  摘要：

  DOI：

  10.1021/ja01637a061

文献信息

• Steroidal Sapogenins. LI. Reaction of Steroidal Olefins with Acetyl Hypobromite^2a,b
  作者：Samuel G. Levine、Monroe E. Wall

  DOI：10.1021/ja01520a052

  日期：1959.6
• Introduction of the 11-Keto Function in the Steroids
  作者：James M. Constantin、L. H. Sarett

  DOI：10.1021/ja01135a059

  日期：1952.8
• Steroidal Sapogenins. XI. Experiments in the Hecogenin Series (Part 2)
  作者：Carl Djerassi、H. Martinez、G. Rosenkranz

  DOI：10.1021/jo50002a015

  日期：1951.8
• Configurational Relationship of 11,12-Oxygenated Sapogenins. Rearrangement to the [3.3.0]Bicycloöctane System¹
  作者：N. L. Wendler、R. F. Hirschmann、H. L. Slates、R. W. Walker

  DOI：10.1021/ja01611a067

  日期：1955.3
• Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies
  作者：Boonsong Kongkathip、Anuch Hasakunpaisarn、Suthinee Boonananwong、Ngampong Kongkathip

  DOI：10.1016/j.steroids.2010.05.003

  日期：2010.12

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogues with different side chains and degrees of oxidation at C-9 were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. (C) 2010 Elsevier Inc. All rights reserved.