(S)-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-7-(5-methyl-4-hexenyl)-1H-indole-3-propanoic acid ethyl ester | 135147-47-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-7-(5-methyl-4-hexenyl)-1H-indole-3-propanoic acid ethyl ester
• CAS: 135147-47-6
• 化学式: C₂₇H₃₉N₃O₅
• 分子量: 485.624
• InChiKey: RQFWGFOAFKKEHX-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  104.22
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-7-(5-methyl-4-hexenyl)-1H-indole-3-propanoic acid ethyl ester 在 sodium tetrahydroborate 、 aluminium amalgam 、 水 、 三乙基铝 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 <2S-(2R^*,5S^*)>-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-9-(5-methyl-4-hexenyl)-3H-pyrrolo<4,3,2-gh>-1,4-benzodiazonin-3-one
  参考文献：
  名称：

  Synthesis of structural analogs of lyngbyatoxin A and their evaluation as activators of protein kinase C

  摘要：

  Syntheses of several new analogues of lyngbyatoxin A from a single common intermediate are described. These compounds bear a carbon chain at the 7-position of the indolactam V (ILV) nucleus which contains either a hydrophilic or a lipophilic group. The effect of these minor structural alterations on the ability of the ILV analogues to activate the enzyme protein kinase C (PKC) was determined by measuring the extent of phosphorylation of calf thymus histone (III-S). Introduction of a hydroxyl group on the C-7 appendage was found to dramatically decrease compound 3's ability to activate PKC. This result is interpreted in terms of the decreased ability of 3 to associate with the membrane bilayer.

  DOI：

  10.1021/jm00112a017
• 作为产物：
  描述：

  N-methyl-N-<7-(4-oxobutyl)-1H-indol-4-yl>-L-valine methyl ester 在 sodium hydride 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-7-(5-methyl-4-hexenyl)-1H-indole-3-propanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of structural analogs of lyngbyatoxin A and their evaluation as activators of protein kinase C

  摘要：

  Syntheses of several new analogues of lyngbyatoxin A from a single common intermediate are described. These compounds bear a carbon chain at the 7-position of the indolactam V (ILV) nucleus which contains either a hydrophilic or a lipophilic group. The effect of these minor structural alterations on the ability of the ILV analogues to activate the enzyme protein kinase C (PKC) was determined by measuring the extent of phosphorylation of calf thymus histone (III-S). Introduction of a hydroxyl group on the C-7 appendage was found to dramatically decrease compound 3's ability to activate PKC. This result is interpreted in terms of the decreased ability of 3 to associate with the membrane bilayer.

  DOI：

  10.1021/jm00112a017