tert-butyl N-[3-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate | 1104804-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: tert-butyl N-[3-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 1104804-44-5
• 化学式: C₃₂H₅₃N₇O₉
• 分子量: 679.814
• InChiKey: HJLFWPWSWPJQGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N1-(3-aminopropyl)-N4-(3-(methyl(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)propyl)butane-1,4-diamine
  参考文献：
  名称：

  Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system

  摘要：

  The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N-1-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.052
• 作为产物：
  描述：

  tert-butyl N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propyl]amino]butyl]carbamate 、 碘甲烷 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以78%的产率得到tert-butyl N-[3-[methyl-(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
  参考文献：
  名称：

  Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system

  摘要：

  The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N-1-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.052

文献信息

• NOUVEAUX DÉRIVÉS FLUORESCENTS DE POLYAMINES, LEUR PROCÉDÉ DE PRÉPARATION ET LEURS APPLICATIONS EN TANT QU'OUTILS DE DIAGNOSTIC DANS LE TRAITEMENT DES TUMEURS CANCÉREUSES.
  申请人：Pierre Fabre Médicament

  公开号：EP2183230B1

  公开（公告）日：2013-11-13
• NOVEL FLUORESCENT DERIVATIVES OF POLYAMINES, METHOD FOR PREPARING SAME AND APPLICATIONS THEREOF AS DIAGNOSIS TOOLS IN THE TREATMENT OF CANCEROUS TUMORS
  申请人：Annereau Jean-Philippe

  公开号：US20100202975A1

  公开（公告）日：2010-08-12

  The invention relates to novel fluorescent derivatives of polyamines having a benzoxadiazole group, to a method for preparing the same and to the use thereof as diagnosis tools for emphasising the polyamine transport system in cancerous cells in order to adapt the treatment thereof, and thus for selecting patients carrying such tumours in order to adapt their treatment. The derivatives are of the formula (I) or a pharmaceutically acceptable salt thereof, in which: R 1 is one or more NO 2 groups in position 4 or 6, or a SO 2 Ph, SO 2 NMe 2 , SO 2 NH 2 or SO 3 H group; R 2 is hydrogen, C 1-6 alkyl, benzyl, a perfluoroalkyl group; the values of a, b, c range from 2 to 5 independently from each other and represent alkylene chains separating the amino groups, and the values of d and e can independently be 0 or 1.
• US8569011B2
  申请人：——

  公开号：US8569011B2

  公开（公告）日：2013-10-29
• Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system
  作者：Yves Guminski、Martial Grousseaud、Sandrine Cugnasse、Viviane Brel、Jean-Philippe Annereau、Stéphane Vispé、Nicolas Guilbaud、Jean-Marc Barret、Christian Bailly、Thierry Imbert

  DOI：10.1016/j.bmcl.2009.03.052

  日期：2009.5

  The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N-1-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS. (c) 2009 Elsevier Ltd. All rights reserved.