(E)-2-(tributylstannyl)-1,4-di(tert-butoxycarbonyl)amino-2-butene

• 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: (E)-2-(tributylstannyl)-1,4-di(tert-butoxycarbonyl)amino-2-butene
• 化学式: C₂₆H₅₂N₂O₄Sn
• 分子量: 575.42
• InChiKey: TXPMSGCAMDYQDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(tributylstannyl)-1,4-di(tert-butoxycarbonyl)amino-2-butene 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到(E)-2-iodo-1,4-di-(tert-butyloxycarbonyl)amino-2-butene
  参考文献：
  名称：

  (Z)-1,4-Diamino-2-butene as a vector of boron, fluorine, or iodine for cancer therapy and imaging: synthesis and biological evaluation

  摘要：

  Polyamine vectors are attractive for tumor targeting. We envisaged (Z)-1,4-diamino-2-butene (Z-DAB), an unsaturated analogue of putrescine Lis vector of B-10. F-18 and I-131 for boron neutron capture therapy (BNCT). and tumor imaging by Positron emission tomography or scintigraphy respectively. In the present work, the synthesis and characterization of new derivatives of Z-DAB were reported. Z-DAB was actively transported in cells via the polyamine transport system and converted into the spermidine analogue. (E)-2-iodo-1,4-diamino-2-butene (E-I-DAB) was not taken up by the polyamine transport system and may not be suitable for tumor imaging. In contrast, (Z)-2-{4-(5,5-dimethyl-[1,3,2]dioxaorinan-2-yl)phenyl}methyl-1,4-diamino-2-butene (Z-4-Bbz-DAB) was a substrate of the transport system and allowed significant boron accumulation in 3LL cells. Its potential in BNCT will be evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00147-5

文献信息

• A new synthetic approach to 2-substituted putrescines
  作者：Caroline Lebarbier、François Carreaux、Bertrand Carboni

  DOI：10.1016/s0040-4039(99)01165-x

  日期：1999.8

  An efficient methodology for the synthesis of 2-substituted putrescines is described. The key step of our approach utilized a coupling reaction of a stereodefined vinylstannane 2, easily derived from 1,4-diaminobut-2-yne 1.

  描述了一种合成2-取代的腐胺的有效方法。我们方法的关键步骤是利用立体定义的乙烯基锡烷2的偶联反应，该反应易于衍生自1,4-二氨基丁-2-炔1。
• (Z)-1,4-Diamino-2-butene as a vector of boron, fluorine, or iodine 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：10.1016/s0968-0896(02)00147-5

  日期：2002.9

  Polyamine vectors are attractive for tumor targeting. We envisaged (Z)-1,4-diamino-2-butene (Z-DAB), an unsaturated analogue of putrescine Lis vector of B-10. F-18 and I-131 for boron neutron capture therapy (BNCT). and tumor imaging by Positron emission tomography or scintigraphy respectively. In the present work, the synthesis and characterization of new derivatives of Z-DAB were reported. Z-DAB was actively transported in cells via the polyamine transport system and converted into the spermidine analogue. (E)-2-iodo-1,4-diamino-2-butene (E-I-DAB) was not taken up by the polyamine transport system and may not be suitable for tumor imaging. In contrast, (Z)-2-4-(5,5-dimethyl-[1,3,2]dioxaorinan-2-yl)phenyl}methyl-1,4-diamino-2-butene (Z-4-Bbz-DAB) was a substrate of the transport system and allowed significant boron accumulation in 3LL cells. Its potential in BNCT will be evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.