(20S)-20-(二甲基氨基)-5alpha-孕甾烷-3beta,4alpha-二醇 | 15112-49-9

• 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
• 中文名称: (20S)-20-(二甲基氨基)-5alpha-孕甾烷-3beta,4alpha-二醇
• 英文名称: terminaline
• 英文别名: (3S,4S,5R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
• CAS: 15112-49-9
• 化学式: C₂₃H₄₁NO₂
• 分子量: 363.584
• InChiKey: QTNGLMWAVBOBLJ-RCFZRFIHSA-N

物化性质

• 熔点：
  243-4°C
• 沸点：
  451.0±15.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20S)-20-(二甲基氨基)-5alpha-孕甾烷-3beta,4alpha-二醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以4.2 mg的产率得到(20S)-20-(dimethylamino)-5α-pregnane-3,4-dione
  参考文献：
  名称：

  Cholinesterase inhibitory pregnane-type steroidal alkaloids from Sarcococca hookeriana

  摘要：

  The bioassay-guided phytochemical investigation on Sarcococca hookeriana have resulted in the isolation of four new pregnane-type steriodal alkaloids: hookerianamide-D [(2 ' E,20S)-20-(N,N-formyl(methyl)amino)-3 beta,-(3 ',4 '-dimethyl-2 '-pentenamido)-5 alpha-pregnane] (1), hookerianamide-E [(2 ' E,20S)-20-(N,N-dimethylamino)-3 beta-(senecioylamino)-5 alpha-pregn-14-en-2 beta-O-acetate] (2), hookerianamide-F [(2 ' E,20S)-20-(N-methylamino)-3 beta-(tigloylamino)-5 alpha-pregn-2,14-dien-4-one] (3), and hookerianamide-G [(20S)-20-(N,N-dimethylamino)-3 beta-(N-methylbenzamido)-5 alpha-pregn-4 beta-O-acetate] (4), along with five known alkaloids 5-9. Their structures were determined by spectroscopic analysis. These steroidal alkaloids and chemically derived derivatives of compound 5 have displayed varying degree of inhibitory activities against acetylcholinesterase and butyrylcholinesterase enzymes in a concentration-dependent fashion, with the IC50 values ranging from 1.5 to 148.2 and 0.6 to 100.2 mu M, respectively. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.11.007

文献信息

• Cholinesterase inhibitory pregnane-type steroidal alkaloids from Sarcococca hookeriana
  作者：M. Iqbal Choudhary、Krishna Prasad Devkota、Sarfraz Ahmad Nawaz、Rosa Ranjit、Atta-ur- Rahman

  DOI：10.1016/j.steroids.2004.11.007

  日期：2005.4

  The bioassay-guided phytochemical investigation on Sarcococca hookeriana have resulted in the isolation of four new pregnane-type steriodal alkaloids: hookerianamide-D [(2 ' E,20S)-20-(N,N-formyl(methyl)amino)-3 beta,-(3 ',4 '-dimethyl-2 '-pentenamido)-5 alpha-pregnane] (1), hookerianamide-E [(2 ' E,20S)-20-(N,N-dimethylamino)-3 beta-(senecioylamino)-5 alpha-pregn-14-en-2 beta-O-acetate] (2), hookerianamide-F [(2 ' E,20S)-20-(N-methylamino)-3 beta-(tigloylamino)-5 alpha-pregn-2,14-dien-4-one] (3), and hookerianamide-G [(20S)-20-(N,N-dimethylamino)-3 beta-(N-methylbenzamido)-5 alpha-pregn-4 beta-O-acetate] (4), along with five known alkaloids 5-9. Their structures were determined by spectroscopic analysis. These steroidal alkaloids and chemically derived derivatives of compound 5 have displayed varying degree of inhibitory activities against acetylcholinesterase and butyrylcholinesterase enzymes in a concentration-dependent fashion, with the IC50 values ranging from 1.5 to 148.2 and 0.6 to 100.2 mu M, respectively. (c) 2005 Elsevier Inc. All rights reserved.