N⁸-acetylspermidine dihydrochloride | 34450-15-2

• 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: N⁸-acetylspermidine dihydrochloride
• 英文别名: N8-Acetylspermidine dihydrochloride；N-[4-(3-aminopropylamino)butyl]acetamide;hydrochloride
• CAS: 34450-15-2
• 化学式: C₉H₂₁N₃O*2ClH
• 分子量: 260.207
• InChiKey: YHLWLRMLRCXNOW-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 溶解度：
  H2O：50 mg/mL，清澈，近乎无色

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  14.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.15
• 氢给体数：
  3.0
• 氢受体数：
  3.0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

制备方法与用途

生物活性

N8-Acetylspermidine dihydrochloride是一种多胺物质。

靶点

Human Endogenous Metabolite

反应信息

• 作为反应物：
  描述：

  N⁸-acetylspermidine dihydrochloride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 1,4-Butanediamine, N-(3-aminopropyl)-N'-ethyl-
  参考文献：
  名称：

  A Comparison of Structure−Activity Relationships between Spermidine and Spermine Analogue Antineoplastics

  摘要：

  A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, spermidine/spermine N-1-acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of-the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N-alpha,N-omega-substituents. It appears that there is an optimum chain length for various activities and that the larger the N-alpha,N-omega-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.

  DOI：

  10.1021/jm960849j
• 作为产物：
  描述：

  N⁸-acetyl-n1-phenylmethoxycarbonylspermidine 在 氢气 作用下， 以70%的产率得到N⁸-acetylspermidine dihydrochloride
  参考文献：
  名称：

  Boukouvalas, John; Golding, Bernard T.; McCabe, Richard W., Angewandte Chemie, 1983, vol. 95, # 8, p. 646 - 647

  摘要：

  DOI：

文献信息

• The Preparation of Spermidine and Monoacetylspermidine
  作者：ERNEST L. JACKSON

  DOI：10.1021/jo01118a010

  日期：1956.12.1