3α,5-cyclo-cholestan-6-one | 7657-63-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α,5-cyclo-cholestan-6-one
• 英文别名: (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]pentacyclo[8.7.0.02,7.05,7.011,15]heptadecan-8-one
• CAS: 7657-63-8
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: PAFPYXSFFACISZ-MOJGUDHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3α,5-cyclo-cholestan-6-one 在 对甲苯磺酸 、 sodium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以79%的产率得到5α-cholest-2-en-6-one
  参考文献：
  名称：

  Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one

  摘要：

  Disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 mu M. respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 mu M). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.005
• 作为产物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-基]甲烷磺酸酯 在 Jones reagent 、 碳酸氢钠 作用下， 以 水 、 丙酮 、 丁酮 为溶剂， 反应 7.0h， 生成 3α,5-cyclo-cholestan-6-one
  参考文献：
  名称：

  Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one

  摘要：

  Disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 mu M. respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 mu M). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.005

文献信息

• SHAFIULLAH;RAFIUDDIN, ANSARI M.;HUSAIN, SHAKIR, BULL. CHEM. SOC. JAP., 60,(1987) N 9, 3411-3414
  作者：SHAFIULLAH、RAFIUDDIN, ANSARI M.、HUSAIN, SHAKIR

  DOI：——

  日期：——
• Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one
  作者：Victoria Richmond、Gustavo A. Garrido Santos、Ana P. Murray、Marta S. Maier

  DOI：10.1016/j.steroids.2011.05.005

  日期：2011.9

  Disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 mu M. respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 mu M). (C) 2011 Elsevier Inc. All rights reserved.