6-{[(1S,10R,11R,13S,14R)-11-Acetoxy-6-hydroxy-1-methoxymethyl-10,13-dimethyl-3,7,17-trioxo-1,7,10,11,12,13,14,15,16,17-decahydro-2-oxa-cyclopenta[a]phenanthren-(4Z)-ylidenemethyl]-methyl-amino}-hexanoic acid | 945383-95-9

• 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: 6-{[(1S,10R,11R,13S,14R)-11-Acetoxy-6-hydroxy-1-methoxymethyl-10,13-dimethyl-3,7,17-trioxo-1,7,10,11,12,13,14,15,16,17-decahydro-2-oxa-cyclopenta[a]phenanthren-(4Z)-ylidenemethyl]-methyl-amino}-hexanoic acid
• 英文别名: 6-[[(Z)-[(3aR,9S,9aR,10R,11aS)-10-acetyloxy-5-hydroxy-9-(methoxymethyl)-9a,11a-dimethyl-1,4,7-trioxo-2,3,3a,9,10,11-hexahydroindeno[4,5-h]isochromen-6-ylidene]methyl]-methylamino]hexanoic acid
• CAS: 945383-95-9
• 化学式: C₃₀H₃₉NO₁₀
• 分子量: 573.64
• InChiKey: HWQASMDRNXGWGS-IUWLPQEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-{[(1S,10R,11R,13S,14R)-11-Acetoxy-6-hydroxy-1-methoxymethyl-10,13-dimethyl-3,7,17-trioxo-1,7,10,11,12,13,14,15,16,17-decahydro-2-oxa-cyclopenta[a]phenanthren-(4Z)-ylidenemethyl]-methyl-amino}-hexanoic acid 在 phosphate buffer 作用下， 以 二甲基亚砜 为溶剂， 生成 渥曼青霉素
  参考文献：
  名称：

  Wortmannin-C20 Conjugates Generate Wortmannin

  摘要：

  We report on C20-6-(N-methylamino)hexanoic conjugates of wortmannin featuring a tertiary enamine attached to the C20 that inhibit phosphoinositol-3-OH kinase (PI3K) by producing wortmannin (Win) through an intramolecular attack. The generation of Win by these conjugates permits the design of Wm based PI3K inhibitors that need not fit into the ATP pocket of PI3K, including Win conjugates of BSA, IgG, or beads. Win generating WmC20-N(Me)-hexanoate conjugates offer an approach to the design of targeted or slow release forms of Win which may inhibit PI3K in tissues more selectively than the parent Win, a compound which has desirable anti-inflammatory and anti-proliferative activities but which also has a variety of toxic effects.

  DOI：

  10.1021/jm050699p
• 作为产物：
  描述：

  6-(methylamino)hexanoic acid hydrochloride 、 渥曼青霉素 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以68.9%的产率得到6-{[(1S,10R,11R,13S,14R)-11-Acetoxy-6-hydroxy-1-methoxymethyl-10,13-dimethyl-3,7,17-trioxo-1,7,10,11,12,13,14,15,16,17-decahydro-2-oxa-cyclopenta[a]phenanthren-(4Z)-ylidenemethyl]-methyl-amino}-hexanoic acid
  参考文献：
  名称：

  Wortmannin-C20 Conjugates Generate Wortmannin

  摘要：

  We report on C20-6-(N-methylamino)hexanoic conjugates of wortmannin featuring a tertiary enamine attached to the C20 that inhibit phosphoinositol-3-OH kinase (PI3K) by producing wortmannin (Win) through an intramolecular attack. The generation of Win by these conjugates permits the design of Wm based PI3K inhibitors that need not fit into the ATP pocket of PI3K, including Win conjugates of BSA, IgG, or beads. Win generating WmC20-N(Me)-hexanoate conjugates offer an approach to the design of targeted or slow release forms of Win which may inhibit PI3K in tissues more selectively than the parent Win, a compound which has desirable anti-inflammatory and anti-proliferative activities but which also has a variety of toxic effects.

  DOI：

  10.1021/jm050699p