N-[(R)-3-(4-Amino-butylamino)-1-methyl-propyl]-acetamide | 875740-02-6

• 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-[(R)-3-(4-Amino-butylamino)-1-methyl-propyl]-acetamide
• 英文别名: Acetamide, N-[(1R)-3-[(4-aminobutyl)amino]-1-methylpropyl]-；N-[(2R)-4-(4-aminobutylamino)butan-2-yl]acetamide
• CAS: 875740-02-6
• 化学式: C₁₀H₂₃N₃O
• 分子量: 201.312
• InChiKey: NCHUZACAGJBRLA-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-(tert-butyloxycarbonyl)-1,8-diamino-5-azanonane 在 盐酸 、 potassium carbonate 、 一水合肼 、 苯硫酚 、 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 21.75h， 生成 N-[(R)-3-(4-Amino-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