N1,N4,N8-Tris(N-methyl-N-(benzyloxy)succinamoyl)spermidine | 117680-01-0

• 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: N1,N4,N8-Tris(N-methyl-N-(benzyloxy)succinamoyl)spermidine
• 英文别名: N¹,N⁴,N⁸-Tris(N-methyl-N-(benzyloxy)succinamoyl)spermidine；N¹,N⁴,N⁸-Tris[N-methyl-N-(benzyloxy)succinamoyl]spermidine
• CAS: 117680-01-0
• 化学式: C₄₃H₅₈N₆O₉
• 分子量: 802.968
• InChiKey: WNBTYMLCKJSNNG-UHFFFAOYSA-N

物化性质

• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  58.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  167.13
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N1,N4,N8-Tris(N-methyl-N-(benzyloxy)succinamoyl)spermidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以83%的产率得到Spermexatin <2,2,2>
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013
• 作为产物：
  描述：

  N-甲基-O-苄基羟胺 在 氢溴酸 、 碳酸氢钠 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 63.0h， 生成 N1,N4,N8-Tris(N-methyl-N-(benzyloxy)succinamoyl)spermidine
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013