(S)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-acetyl-1,8-diamino-5-azanonane | 875681-04-2

• 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: (S)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-acetyl-1,8-diamino-5-azanonane
• 英文别名: N-[(2S)-4-[4-(1,3-dioxoisoindol-2-yl)butyl-(2-nitrophenyl)sulfonylamino]butan-2-yl]acetamide
• CAS: 875681-04-2
• 化学式: C₂₄H₂₈N₄O₇S
• 分子量: 516.575
• InChiKey: BPDUQRFNFLQLLQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-acetyl-1,8-diamino-5-azanonane 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-{(S)-3-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butylamino]-1-methyl-propyl}-acetamide
  参考文献：
  名称：

  α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase

  摘要：

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.

  DOI：

  10.1021/jm050872h
• 作为产物：
  描述：

  (S)-N¹-(o-nitrophenylsulfonyl)-N³-(tert-butyloxycarbonyl)-1,3-diaminobutane 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 (S)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-acetyl-1,8-diamino-5-azanonane
  参考文献：
  名称：

  α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase

  摘要：

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.

  DOI：

  10.1021/jm050872h

文献信息

• α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase
  作者：Aki J. Järvinen、Marc Cerrada-Gimenez、Nikolay A. Grigorenko、Alex R. Khomutov、Jouko J. Vepsäläinen、Riitta M. Sinervirta、Tuomo A. Keinänen、Leena I. Alhonen、Juhani E. Jänne

  DOI：10.1021/jm050872h

  日期：2006.1.1

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.