(5aS,7S)-7-[1-[[4-(hydroxymethyl)phenyl]methylamino]propan-2-yl]-3-methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one | 1402353-97-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5aS,7S)-7-[1-[[4-(hydroxymethyl)phenyl]methylamino]propan-2-yl]-3-methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one
• CAS: 1402353-97-2
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: VOSGBTIUAVXGTR-WWIHDFJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5aS,7S)-7-[1-[[4-(hydroxymethyl)phenyl]methylamino]propan-2-yl]-3-methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以64%的产率得到4-[[2-[(5aS,7S)-3-methyl-1-oxo-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-7-yl]propylamino]methyl]benzaldehyde
  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
• 作为产物：
  描述：

  对羟基甲基苯甲醛 、 (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)-7-[1-[[4-(hydroxymethyl)phenyl]methylamino]propan-2-yl]-3-methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one
  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

文献信息

• 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
  作者：Laxman Pokhrel、Izumi Maezawa、Thi D. T. Nguyen、Kyeong-Ok Chang、Lee-Way Jin、Duy H. Hua

  DOI：10.1021/jm3012189

  日期：2012.10.25

  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.