N-[20S-(dimethylamino)-16α-hydroxy-4β,14α-dimethyl-4α-[(methylamino)methyl]-11-oxo-9,19-cyclo-5α,9β-pregnan-3β-yl]-isobutyramide | 1310344-12-7

• 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: N-[20S-(dimethylamino)-16α-hydroxy-4β,14α-dimethyl-4α-[(methylamino)methyl]-11-oxo-9,19-cyclo-5α,9β-pregnan-3β-yl]-isobutyramide
• CAS: 1310344-12-7
• 化学式: C₃₁H₅₃N₃O₃
• 分子量: 515.78
• InChiKey: GENPTQIVBQAUTL-YRGUKJKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.67
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[20S-(dimethylamino)-16α-hydroxy-4β,14α-dimethyl-4α-[(methylamino)methyl]-11-oxo-9,19-cyclo-5α,9β-pregnan-3β-yl]-isobutyramide 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 以80%的产率得到20S-(dimethylamino)-16α-hydroxy-4β,14α-dimethyl-9,19-cyclo-{2'-isopropyl-1'-methyl-1',4'α,5',6'-tetrahydro-pyrimidino[4',5':3,4]}-5α,9β-pregnan-11-one
  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：

  N-[(3β,4α,5α,9β,16β)-20-(dimethylamino)-4-formyl-16-hydroxy-4,14-dimethyl-11-oxo-9,19-cyclopregnan-3-yl]-2-methylpropanamide 在 sodium cyanoborohydride 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 N-[20S-(dimethylamino)-16α-hydroxy-4β,14α-dimethyl-4α-[(methylamino)methyl]-11-oxo-9,19-cyclo-5α,9β-pregnan-3β-yl]-isobutyramide
  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