N¹-acetylspermidine dihydrochloride | 34450-16-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N¹-acetylspermidine dihydrochloride
• 英文别名: N-[3-(4-aminobutylamino)propyl]acetamide;hydrochloride
• CAS: 34450-16-3
• 化学式: C₉H₂₁N₃O*2ClH
• 分子量: 260.207
• InChiKey: BNLLYRAFRFKJEA-UHFFFAOYSA-N

物化性质

• 熔点：
  184-188°C
• 溶解度：
  可溶于甲醇（轻微加热）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.2
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

N1-Acetylspermidine hydrochloride 是多胺的乙酰衍生物。N1-Acetylspermidine hydrochloride是多胺氧化酶 (PAO) 的底物。N1-Acetylspermidine hydrochloride 选择性升高人结直肠癌中的N1-乙酰亚精胺水平。N1-Acetylspermidine hydrochloride 在 DNA 的无嘌呤位点上具有一定的切割效率。

反应信息

• 作为反应物：
  描述：

  N¹-acetylspermidine dihydrochloride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 N'-[3-(乙胺基)丙基]丁烷-1,4-二胺
  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：

  3-acetamidopropanal 在 sodium tetrahydroborate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 N¹-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：