(5aS,7S)-3-methyl-7-{1-[(4-hydroxynaphthalen-1-yl)methylamino]propan-2-yl}-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran trifluoroacetate | 1402354-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5aS,7S)-3-methyl-7-{1-[(4-hydroxynaphthalen-1-yl)methylamino]propan-2-yl}-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran trifluoroacetate
• CAS: 1402354-20-4
• 化学式: C₂HF₃O₂*C₂₇H₂₉NO₄
• 分子量: 545.556
• InChiKey: WMNINQVQAYHTLI-SFLARJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  109.0
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-羟基-1-萘甲醛 、 三氟乙酸 、 (5aS,7S)-7-(2-amino-1-methylethyl)-3-methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 (5aS,7S)-3-methyl-7-{1-[(4-hydroxynaphthalen-1-yl)methylamino]propan-2-yl}-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran trifluoroacetate
  参考文献：
  名称：

  Inhibition of Acyl-CoA: Cholesterol Acyltransferase (ACAT), Overexpression of Cholesterol Transporter Gene, and Protection of Amyloid β (Aβ) Oligomers-Induced Neuronal Cell Death by Tricyclic Pyrone Molecules

  摘要：

  A major effort in Alzheimer's disease therapeutic development has targeted A beta and downstream :vents. We have synthesized a small library of tricyclic pyrone compounds. Their protective action in MC65 cells and inhibition of ACAT along with the upregulation of cholesterol transporter gene were investigated. Five active compounds exhibited potencies in the nanomolar ranges. The multiple effects of the compounds on A beta and cellular cholesterol pathways could be potential mechanisms underlying the protective effects in vivo.

  DOI：

  10.1021/jm3012189