3β-[(tert-butoxycarbonyl)amino]-20S-(dimethylamino)-4α-formyl-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate | 1310344-22-9

• 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
• 英文名称: 3β-[(tert-butoxycarbonyl)amino]-20S-(dimethylamino)-4α-formyl-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate
• CAS: 1310344-22-9
• 化学式: C₃₈H₅₄N₂O₆
• 分子量: 634.857
• InChiKey: IUDPVAQNBFYENC-FLMIIEFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  46.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-甲基-2-丁酮 、 3β-[(tert-butoxycarbonyl)amino]-20S-(dimethylamino)-4α-formyl-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate 在 lithium diisopropyl amide 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 3.25h， 以79%的产率得到3β-[(tert-butoxycarbonyl)amino]-20S-(dimethylamino)-4α-(1-hydroxy-4-methyl-3-oxopentyl)-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate
  参考文献：
  名称：

  New potent human acetylcholinesterase inhibitors in the tetracyclic triterpene series with inhibitory potency on amyloid β aggregation

  摘要：

  New acetylcholinesterase inhibitors in the tetracyclic triterpene series were synthesized, tested in vitro for the inhibition of cholinesterases (different sources of AChE and BuChE) and for the ability to prevent AChE-induced A beta aggregation. Some compounds have hAChE IC50 values in the nanomolar range and showed ability to block the AChE-induced A beta aggregation. The mode of interaction between EeAChE and compounds 1 and 36e was investigated using docking and molecular dynamics simulations. These studies suggested that both compounds interact simultaneously with the catalytic and the peripheral sites of AChE, and the nature of protein-ligand interactions is mainly hydrophobic. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.073
• 作为产物：
  描述：

  (3β,4α,9β,16α,20S)-3-amino-20-(dimethylamino)-16-hydroxy-4-(hydroxymethyl)-4,14-dimethyl-9,19-cyclopregnan-11-one 在 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 三甲胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 3β-[(tert-butoxycarbonyl)amino]-20S-(dimethylamino)-4α-formyl-4β,14α-dimethyl-11-oxo-9,19-cyclo-5α,9β-pregnan-16α-yl benzoate
  参考文献：
  名称：

  New potent human acetylcholinesterase inhibitors in the tetracyclic triterpene series with inhibitory potency on amyloid β aggregation

  摘要：

  New acetylcholinesterase inhibitors in the tetracyclic triterpene series were synthesized, tested in vitro for the inhibition of cholinesterases (different sources of AChE and BuChE) and for the ability to prevent AChE-induced A beta aggregation. Some compounds have hAChE IC50 values in the nanomolar range and showed ability to block the AChE-induced A beta aggregation. The mode of interaction between EeAChE and compounds 1 and 36e was investigated using docking and molecular dynamics simulations. These studies suggested that both compounds interact simultaneously with the catalytic and the peripheral sites of AChE, and the nature of protein-ligand interactions is mainly hydrophobic. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.073