5-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enylamino]-naphthalene-1-sulfonic acid methyl-(4-methyl-pent-3-enyl)-amide | 798573-73-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enylamino]-naphthalene-1-sulfonic acid methyl-(4-methyl-pent-3-enyl)-amide
• 英文别名: 5-[[(E)-4-[tert-butyl(dimethyl)silyl]oxy-2-methylbut-2-enyl]amino]-N-methyl-N-(4-methylpent-3-enyl)naphthalene-1-sulfonamide
• CAS: 798573-73-6
• 化学式: C₂₈H₄₄N₂O₃SSi
• 分子量: 516.82
• InChiKey: NAVMNGMDGOHTQC-PTGBLXJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enylamino]-naphthalene-1-sulfonic acid methyl-(4-methyl-pent-3-enyl)-amide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以41%的产率得到5-((E)-4-Hydroxy-2-methyl-but-2-enylamino)-naphthalene-1-sulfonic acid methyl-(4-methyl-pent-3-enyl)-amide
  参考文献：
  名称：

  Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues

  摘要：

  New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.

  DOI：

  10.1021/jo049101w
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.09h， 生成 5-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enylamino]-naphthalene-1-sulfonic acid methyl-(4-methyl-pent-3-enyl)-amide
  参考文献：
  名称：

  Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues

  摘要：

  New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.

  DOI：

  10.1021/jo049101w

文献信息

• Synthesis and Activity of Fluorescent Isoprenoid Pyrophosphate Analogues
  作者：Kim、Troy S. Kleckley、Andrew J. Wiemer、Sarah A. Holstein、Raymond J. Hohl、David F. Wiemer

  DOI：10.1021/jo049101w

  日期：2004.11.1

  New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.