N-(4-aminobutyl)-4-nitrobenzamide | 455251-67-9

• 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: N-(4-aminobutyl)-4-nitrobenzamide
• CAS: 455251-67-9
• 化学式: C₁₁H₁₅N₃O₃
• 分子量: 237.258
• InChiKey: DFAVLHWHASUGGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-aminobutyl)-4-nitrobenzamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯酚 为溶剂， 反应 7.0h， 生成 6-amino-9-[11-(N-(4-(4-nitrobenzamido)butyl)acridin-9-yl-4-carboxamido)-3,7,11-triazaundecyl]-9H-purine trihydrochloride
  参考文献：
  名称：

  Design of site specific DNA damaging agents for generation of multiply damaged sites

  摘要：

  We describe the synthesis and DNA damaging activities of hybrid molecules in which a purine (adenine) is linked to an intercalating chromophore (acridine) by a polyamino linker. A DNA damaging agent, phenanthroline or para-nitrobenzamide, is tethered to the acridine moiety at various positions. Our goal is to induce upon activation other lesions in close proximity to the abasic site and therefore create cytotoxic multiply damaged sites. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00345-9
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 四亚甲基二胺 在 N-甲基吗啉 、 Wang resin-OCOO-p-nitrophenyl 、 三氟乙酸 作用下， 生成 N-(4-aminobutyl)-4-nitrobenzamide
  参考文献：
  名称：

  Solid phase organic synthesis of polyamine derivatives and initial biological evaluation of their antitumoral activity

  摘要：

  A series of N-1-monosubstituted putrescine and spermine derivatives was synthesised using a solid phase methodology. We evaluated their cytotoxicity, calmodulin antagonism and polyamine uptake inhibition, pharmacological. properties shared by some antitumoral agents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00086-9

文献信息

• A Novel and Practical Synthesis of Mavorixafor
  作者：Weiyuan Liu、Siju Bi、Ting Tian、Ting Zhou、Kuaile Lin、Weicheng Zhou

  DOI：10.1021/acs.oprd.2c00076

  日期：2022.6.17

  A novel and practical synthesis of mavorixafor (1) is reported. The novelty of this synthetic route is the use of 8-chloro-5,6,7,8-tetrahydroquinoline (9) and 1,4-diaminobutane as the materials, instead of 8-amino-5,6,7,8-tetrahydroquinoline (4) and N,N-diprotected aminobutyraldehyde (6a or 6b). The preparation of (S)-8-(4-aminobutylamino)-5,6,7,8-tetrahydroquinoline (13) by resolution with N-acetyl-l-leucine

  报道了一种新颖实用的 mavorixafor ( 1 ) 合成方法。该合成路线的新颖之处在于以8-氯-5,6,7,8-四氢喹啉（9）和1,4-二氨基丁烷为原料，代替了8-氨基-5,6,7,8-四氢喹啉 ( 4 ) 和 N,N-二保护氨基丁醛 ( 6a或6b )。首次实现了N-乙酰-l-亮氨酸拆分制备( S )-8-(4-氨基丁基氨基)-5,6,7,8-四氢喹啉( 13 )。然后从13一锅合成1成功开发了涉及保护、缩合和后续水解的技术。此外，通过简单的操作（成盐），无需柱色谱纯化，即可获得纯度令人满意的最终产品（>99.5%，通过非手性和手性 HPLC 检测）。
• Design of site specific DNA damaging agents for generation of multiply damaged sites
  作者：Alain Martelli、Jean-Francois Constant、Martine Demeunynck、Jean Lhomme、Pascal Dumy

  DOI：10.1016/s0040-4020(02)00345-9

  日期：2002.5

  We describe the synthesis and DNA damaging activities of hybrid molecules in which a purine (adenine) is linked to an intercalating chromophore (acridine) by a polyamino linker. A DNA damaging agent, phenanthroline or para-nitrobenzamide, is tethered to the acridine moiety at various positions. Our goal is to induce upon activation other lesions in close proximity to the abasic site and therefore create cytotoxic multiply damaged sites. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Solid phase organic synthesis of polyamine derivatives and initial biological evaluation of their antitumoral activity
  作者：Sophie Tomasi、Myriam Le Roch、Jacques Renault、Jean-Charles Corbel、Philippe Uriac、Bertrand Carboni、Damien Moncoq、Bénedicte Martin、Jean-Guy Delcros

  DOI：10.1016/s0960-894x(98)00086-9

  日期：1998.3

  A series of N-1-monosubstituted putrescine and spermine derivatives was synthesised using a solid phase methodology. We evaluated their cytotoxicity, calmodulin antagonism and polyamine uptake inhibition, pharmacological. properties shared by some antitumoral agents. (C) 1998 Elsevier Science Ltd. All rights reserved.