N⁴-Benzyl-N¹,N⁸-bisspermidine | 83392-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴-Benzyl-N¹,N⁸-bisspermidine
• 英文别名: tert-butyl N-{4-{N-{3-[(tert-butyloxycarbonyl)amino]propyl}(phenylmethyl)amino}butyl}carbamate；N⁴-Benzyl-N¹,N⁸-bis[t-butoxycarbonyl]spermidine；tert-butyl N-[3-[benzyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]propyl]carbamate
• CAS: 83392-08-9
• 化学式: C₂₄H₄₁N₃O₄
• 分子量: 435.607
• InChiKey: YWKHYRFHRLLLMF-UHFFFAOYSA-N

物化性质

• 沸点：
  556.9±40.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-Benzyl-N¹,N⁸-bisspermidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 12.0h， 生成 N¹,N⁸-Bis(tert-butoxycarbonyl)-N⁴-[2''-hydroxy-3''-(2'-nitroimidazol-1'-yl)propyl]spermidine
  参考文献：
  名称：

  Synthesis of a novel nitroimidazole-spermidine derivative as a tumor-targeted hypoxia-selective cytotoxin

  摘要：

  A four-step synthesis of (R,S)-N-4-[3-(2-nitro-1-imidazolyl)-2-hydroxypropyl]-spermidine trihydrochloride (4) is described and the utilization of the polyamine active transport system for the uptake of this compound in cells is demonstrated. Thus, V79 cells pretreated with an inhibitor of spermidine biosynthesis, alpha-difluoromethylornithine (DFMO), are ca. 2-fold more sensitive to 4 under hypoxic conditions, compared to untreated cells. Similarly, radiosensitization of hypoxic V79 cells by 4 is improved in DFMO-pretreated cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.100
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-(3-aminobutyl)-N-(3-aminopropyl)(phenylmethyl)amine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到N⁴-Benzyl-N¹,N⁸-bisspermidine
  参考文献：
  名称：

  Synthesis of a novel nitroimidazole-spermidine derivative as a tumor-targeted hypoxia-selective cytotoxin

  摘要：

  A four-step synthesis of (R,S)-N-4-[3-(2-nitro-1-imidazolyl)-2-hydroxypropyl]-spermidine trihydrochloride (4) is described and the utilization of the polyamine active transport system for the uptake of this compound in cells is demonstrated. Thus, V79 cells pretreated with an inhibitor of spermidine biosynthesis, alpha-difluoromethylornithine (DFMO), are ca. 2-fold more sensitive to 4 under hypoxic conditions, compared to untreated cells. Similarly, radiosensitization of hypoxic V79 cells by 4 is improved in DFMO-pretreated cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.100

文献信息

• <i>N</i>-Benzylpolyamines as Vectors of Boron and Fluorine for Cancer Therapy and Imaging:  Synthesis and Biological Evaluation
  作者：Bénédicte Martin、Françoise Possémé、Caroline Le Barbier、François Carreaux、Bertrand Carboni、Nikolaus Seiler、Jacques-Philippe Moulinoux、Jean-Guy Delcros

  DOI：10.1021/jm010897q

  日期：2001.10.1

  N-benzyl derivatives of the polyamines as vectors of (10)B and (18)F for boron neutron capture therapy (BNCT) and tumor imaging by positron emission tomography (PET), respectively. In the present work, the synthesis, transport characteristics, DNA-binding properties, and cytotoxicity of several N-benzyl derivatives of putrescine and spermidine are described. The fluorinated spermidine derivative N-(3-

  癌细胞具有高亲和力的多胺吸收系统，但结构特征的严格性较低。因此，腐胺，亚精胺和亚精胺被认为是在治疗或诊断上有用的结构和元件在肿瘤中选择性积累的潜在载体。我们设想多胺的N-苄基衍生物分别作为（10）B和（18）F的载体，用于硼中子俘获治疗（BNCT）和通过正电子发射断层扫描（PET）进行肿瘤成像。在本工作中，描述了几种腐胺和亚精胺的N-苄基衍生物的合成，转运特性，DNA结合特性和细胞毒性。氟化亚精胺衍生物N-（3-[（[4-氨基丁基）氨基]丙基）[（4-氟苯基）甲基]胺（N（1）-4-Fbz-spd）可能因其高积累而用于PET通过多胺转运系统在癌细胞中 在含硼的苄基多胺中，N-（4-氨基丁基）（[4-（二羟基硼基）苯基]甲基）胺（4-Bbz-put）和N-（3-[（4-氨基丁基）氨基]丙基） （[4-（二羟基硼基）苯基]甲基）胺（N（1）-4-Bbz-spd）应该适用于BNCT，因为它们在B
• Bergeron, R. J.; Stolowich, N.J., Synthesis, 1982, # 8, p. 689 - 691
  作者：Bergeron, R. J.、Stolowich, N.J.

  DOI：——

  日期：——