N-(4-dipropylaminobutyl)-4-pyrrolidinotriazenylbenzamide | 216752-14-6

• 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: N-(4-dipropylaminobutyl)-4-pyrrolidinotriazenylbenzamide
• 英文别名: N-[4-(dipropylamino)butyl]-4-(pyrrolidin-1-yldiazenyl)benzamide
• CAS: 216752-14-6
• 化学式: C₂₁H₃₅N₅O
• 分子量: 373.542
• InChiKey: BGNMAXYBAJJZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-dipropylaminobutyl)-4-pyrrolidinotriazenylbenzamide 在 sodium iodide 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 N-(4-dipropylaminobutyl)-4-[125I]-iodobenzamide
  参考文献：
  名称：

  Radiosynthesis of no-carrier-added N-(4-dipropyl aminobutyl)-4-[125I]-iodobenzamide, a promising tracer for the detection of melanoma

  摘要：

  N-(4-dipropylaminobutyl)-4-iodobenzamide was recently developed in our laboratory as a potentially improved imaging agent for metastatic melanoma. Our purpose was to seek an efficient route to the labelling of this tracer with iodine-125 at a carrier free level. Three different approaches were explored : Wallach triazene reaction, nucleophilic exchange of bromide for iodide, iododestannylation. The most suitable method appeared to be the electrophilic radio-iododestannylation of the tributyl-stannyl precursor using no-carrier added sodium [I-125] iodide oxidized with chloramine T. The exchange between iodine-125 and the leaving group occurred in 15 min at room temperature. A chemically and radiochemically pure product was obtained after reverse phase HPLC purification, with a radiolabeling yield of about 75%.

  DOI：

  10.1002/(sici)1099-1344(1998100)41:10<965::aid-jlcr141>3.0.co;2-y
• 作为产物：
  描述：

  N1,N1-dipropylbutane-1,4-diamine 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 N-(4-dipropylaminobutyl)-4-pyrrolidinotriazenylbenzamide
  参考文献：
  名称：

  Radiosynthesis of no-carrier-added N-(4-dipropyl aminobutyl)-4-[125I]-iodobenzamide, a promising tracer for the detection of melanoma

  摘要：

  N-(4-dipropylaminobutyl)-4-iodobenzamide was recently developed in our laboratory as a potentially improved imaging agent for metastatic melanoma. Our purpose was to seek an efficient route to the labelling of this tracer with iodine-125 at a carrier free level. Three different approaches were explored : Wallach triazene reaction, nucleophilic exchange of bromide for iodide, iododestannylation. The most suitable method appeared to be the electrophilic radio-iododestannylation of the tributyl-stannyl precursor using no-carrier added sodium [I-125] iodide oxidized with chloramine T. The exchange between iodine-125 and the leaving group occurred in 15 min at room temperature. A chemically and radiochemically pure product was obtained after reverse phase HPLC purification, with a radiolabeling yield of about 75%.

  DOI：

  10.1002/(sici)1099-1344(1998100)41:10<965::aid-jlcr141>3.0.co;2-y

文献信息

• Radiosynthesis of no-carrier-added N-(4-dipropyl aminobutyl)-4-[125I]-iodobenzamide, a promising tracer for the detection of melanoma
  作者：M. F. Moreau、P. Labarre、A. Foucaud、H. Seguin、M. Bayle、J. Papon、J. C. Madelmont

  DOI：10.1002/(sici)1099-1344(1998100)41:10<965::aid-jlcr141>3.0.co;2-y

  日期：1998.10

  N-(4-dipropylaminobutyl)-4-iodobenzamide was recently developed in our laboratory as a potentially improved imaging agent for metastatic melanoma. Our purpose was to seek an efficient route to the labelling of this tracer with iodine-125 at a carrier free level. Three different approaches were explored : Wallach triazene reaction, nucleophilic exchange of bromide for iodide, iododestannylation. The most suitable method appeared to be the electrophilic radio-iododestannylation of the tributyl-stannyl precursor using no-carrier added sodium [I-125] iodide oxidized with chloramine T. The exchange between iodine-125 and the leaving group occurred in 15 min at room temperature. A chemically and radiochemically pure product was obtained after reverse phase HPLC purification, with a radiolabeling yield of about 75%.