N-<4-<(carbobenzyloxy)amino>butyl>phthalimide | 66917-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<4-<(carbobenzyloxy)amino>butyl>phthalimide
• 英文别名: (4-phthalimido-butyl)-carbamic acid benzyl ester；N-Benzyloxycarbonyl-N'-phthaloyl-1,4-butandiamin；Carbamic acid, [4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]-, phenylmethyl ester；benzyl N-[4-(1,3-dioxoisoindol-2-yl)butyl]carbamate
• CAS: 66917-07-5
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: ILXIPUPINWDQKO-UHFFFAOYSA-N

物化性质

• 沸点：
  549.1±43.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-<4-<(carbobenzyloxy)amino>butyl>phthalimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N-(苄氧羰基)-1,4-丁二胺
  参考文献：
  名称：

  合成冯苏-顺/苏-反-和-赤-顺/赤-反-二氢palustrin。17. MitteilungüberSchachtelhalmalkaloide † ‡

  摘要：

  合成苏-顺/苏-反式-和赤-顺/赤-反式-dihydropalustrin

  DOI：

  10.1002/hlca.19780610240
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 palladium dihydroxide N-甲基吗啉 、 盐酸 、 sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~57.0 ℃ 、220.64 kPa 条件下， 反应 66.0h， 生成 N-<4-<(carbobenzyloxy)amino>butyl>phthalimide
  参考文献：
  名称：

  .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines

  摘要：

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.

  DOI：

  10.1021/jm00082a013

文献信息

• Synthese von<i>threo</i>-<i>cis</i>/<i>threo</i>-<i>trans</i>- und<i>erythro</i>-<i>cis</i>/<i>erythro</i>-<i>trans</i>-Dihydropalustrin. 17. Mitteilung über Schachtelhalmalkaloide
  作者：Elisabeth Wälchli-Schaer、Conrad Hans Eugster

  DOI：10.1002/hlca.19780610240

  日期：1978.3.8

  Synthesis of threo-cis/threo-trans- and erythro-cis/erythro-trans-dihydropalustrin

  合成苏-顺/苏-反式-和赤-顺/赤-反式-dihydropalustrin
• .alpha.-Methyl polyamines: metabolically stable spermidine and spermine mimics capable of supporting growth in cells depleted of polyamines
  作者：John R. Lakanen、James K. Coward、Anthony E. Pegg

  DOI：10.1021/jm00082a013

  日期：1992.2

  In order to assess the tolerance of the target enzyme spermine synthase for alpha-substituents on the aminopropyl moiety of the substrate spermidine, 1-methylspermidine (MeSpd, 2) was synthesized. It was determined that MeSpd is a poor substrate for spermine synthase and is not a substrate for spermidine N1-acetyltransferase, suggesting that alpha-methylated polyamines might be metabolically stable and therefore useful tools for studying polyamine effects in intact cells. On the basis of initial cellular results with 2, 1-methylspermine (MeSpm, 3) and 1,12-dimethylspermine (Me2Spm, 4) were also synthesized. When added to cells (L1210, SV-3T3, or HT29) depleted of both putrescine and spermidine by prior treatment with alpha-(difluoromethyl)ornithine (DFMO), these alpha-methylated polyamines were able to restore cell growth to that observed in the absence of DFMO. In accord with the enzyme data noted above, metabolic studies indicated a slow conversion of 2 to 3, but no metabolism of 4 in these cells. It was concluded from these results that the alpha-methylated polyamines are able to substitute for the natural polyamines spermidine and spermine in critical biochemical processes which involve polyamines for continued cell growth. In accord with the hypothesis, preliminary data indicate that MeSpd and Me2Spm are as effective as spermidine and spermine, respectively, in promoting the conversion of B-DNA to Z-DNA.