N-<<<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-4,5-dihydro-5-isoxazolyl><1--1H-pyrrol-3-yl>methyl>-L-valine methyl ester | 135454-73-8

• 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: N-<<<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-4,5-dihydro-5-isoxazolyl><1--1H-pyrrol-3-yl>methyl>-L-valine methyl ester
• 英文别名: methyl (2S)-2-[[[3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-4,5-dihydro-1,2-oxazol-5-yl]-[1-tri(propan-2-yl)silylpyrrol-3-yl]methyl]amino]-3-methylbutanoate
• CAS: 135454-73-8
• 化学式: C₃₃H₆₃N₃O₄Si₂
• 分子量: 622.052
• InChiKey: NNUMSAYJFAHUKF-HRONLVMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-<<<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-4,5-dihydro-5-isoxazolyl><1--1H-pyrrol-3-yl>methyl>-L-valine methyl ester 在 W-2 Raney nickel 咪唑 、 sodium tetrahydroborate 、 aluminium amalgam 、 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 、 sodium carbonate 、 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.58h， 生成 (RS)-N-<3-(2-amino-3-hydroxypropyl)-7-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-1H-indol-4-yl>-N-methyl-L-valine methyl 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
• 作为产物：
  描述：

  在 咪唑 、 硫酸 、 叔丁基锂 、 magnesium sulfate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.33h， 生成 N-<<<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>butyl>-4,5-dihydro-5-isoxazolyl><1--1H-pyrrol-3-yl>methyl>-L-valine methyl 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

文献信息

• KOZIKOWSKI, ALAN P.;SHUM, PATRICK W.;BASU, ALAKANANDA;LAZO, JOHN S., J. MED. CHEM., 34,(1991) N, C. 2420-2430
  作者：KOZIKOWSKI, ALAN P.、SHUM, PATRICK W.、BASU, ALAKANANDA、LAZO, JOHN S.

  DOI：——

  日期：——