(S)-7-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-1H-indole-3-propanoic acid ethyl ester | 135147-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-7-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-1H-indole-3-propanoic acid ethyl ester
• CAS: 135147-45-4
• 化学式: C₃₀H₄₉N₃O₆Si
• 分子量: 575.821
• InChiKey: WWPQEDZBADEWPI-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  113.45
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-7-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-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^*)>-9-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-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：

  methyl (2S)-2-[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]methylideneamino]-3-methylbutanoate 在 W-2 Raney nickel 咪唑 、 dimethyl sulfide borane 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 、 水 、 氢气 、 叔丁基锂 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.91h， 生成 (S)-7-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-α-(hydroxyimino)-4-<<1-(methoxycarbonyl)-2-methylpropyl>methylamino>-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