3,7,12,20-tetrakis(2-nitrobenzenesulfonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1(26),12(27),15,17,22,24-hexaene | 211512-26-4

• 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: 3,7,12,20-tetrakis(2-nitrobenzenesulfonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1(26),12(27),15,17,22,24-hexaene
• 英文别名: 3,11,15,20-Tetrakis[(2-nitrophenyl)sulfonyl]-3,11,15,20,26,27-hexazatricyclo[20.3.1.15,9]heptacosa-1(25),5,7,9(27),22(26),23-hexaene
• CAS: 211512-26-4
• 化学式: C₄₅H₄₄N₁₀O₁₆S₄
• 分子量: 1109.17
• InChiKey: MIPFHADKZOZGHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  75
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  392
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  3,7,12,20-tetrakis(2-nitrobenzenesulfonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1(26),12(27),15,17,22,24-hexaene 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1(26),12(27),15,17,22,24-hexaene
  参考文献：
  名称：

  Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries

  摘要：

  Six novel, asymmetric, 19- to 26-membered polyazadipyridinocyclophane scaffolds 1-6 have been synthesized in high yields by an efficient cyclization of ditosylate 39 with the appropriate six fully protected triamines 40-45, followed by removing the 2-nitrobenzenesulfonyl protecting groups. intermediate 39 was synthesized by the Mitsunobu reaction of 2-nitrobenzenesulfonamide (37) with 2,6-pyridinedimethanol (36), and a subsequent tosylation of the resulted diol 38. The fully protected asymmetric triamines 41 and 43 were prepared from the corresponding commercially available triamines 52 and 53. A new synthetic route was developed for the synthesis of the protected asymmetric triamines 44 and 45. Ah reactions were carried out at room temperature in high yields. The reaction of t-Boc-protected scaffold 1, having three reactive sites, with nine benzylic bromides and bromoacetonitrile, using a solution phase simultaneous addition of functionalities combinatorial strategy, Save t-Boc-protected library 7 containing 1000 compounds. Deprotection of library 7 generated the intermediate library 8 with one reactive site. Subsequent reactions at the unsubstituted position of 8 with various functionalities by four types of reactions gave sixteen final libraries 9-24. Libraries 7-24 have different functionalities at the fixed position, and each of them contains 1000 compounds. The reaction of scaffold 2, having four reactive sites without protecting groups, with six sets of polar functionalities afforded eleven diverse libraries 25-35 containing 625 compounds in each library. Totally, twenty-nine libraries containing 24875 compounds were obtained. Eight libraries exhibited antibacterial activity against Escherichia coli imp(-) and Streptococcus pyogenes with the MIC's of 2 to 10-50 mu M. Seven libraries disrupted HIV-1 tat/TAR protein-RNA interactions with IC50's as low as 0.08 mu M. (C) 1998 Elsevier Science Ltd.All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00441-4
• 作为产物：
  描述：

  2-硝基苯磺酰胺 在 sodium hydroxide 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 3,7,12,20-tetrakis(2-nitrobenzenesulfonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1(26),12(27),15,17,22,24-hexaene
  参考文献：
  名称：

  Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries

  摘要：

  Six novel, asymmetric, 19- to 26-membered polyazadipyridinocyclophane scaffolds 1-6 have been synthesized in high yields by an efficient cyclization of ditosylate 39 with the appropriate six fully protected triamines 40-45, followed by removing the 2-nitrobenzenesulfonyl protecting groups. intermediate 39 was synthesized by the Mitsunobu reaction of 2-nitrobenzenesulfonamide (37) with 2,6-pyridinedimethanol (36), and a subsequent tosylation of the resulted diol 38. The fully protected asymmetric triamines 41 and 43 were prepared from the corresponding commercially available triamines 52 and 53. A new synthetic route was developed for the synthesis of the protected asymmetric triamines 44 and 45. Ah reactions were carried out at room temperature in high yields. The reaction of t-Boc-protected scaffold 1, having three reactive sites, with nine benzylic bromides and bromoacetonitrile, using a solution phase simultaneous addition of functionalities combinatorial strategy, Save t-Boc-protected library 7 containing 1000 compounds. Deprotection of library 7 generated the intermediate library 8 with one reactive site. Subsequent reactions at the unsubstituted position of 8 with various functionalities by four types of reactions gave sixteen final libraries 9-24. Libraries 7-24 have different functionalities at the fixed position, and each of them contains 1000 compounds. The reaction of scaffold 2, having four reactive sites without protecting groups, with six sets of polar functionalities afforded eleven diverse libraries 25-35 containing 625 compounds in each library. Totally, twenty-nine libraries containing 24875 compounds were obtained. Eight libraries exhibited antibacterial activity against Escherichia coli imp(-) and Streptococcus pyogenes with the MIC's of 2 to 10-50 mu M. Seven libraries disrupted HIV-1 tat/TAR protein-RNA interactions with IC50's as low as 0.08 mu M. (C) 1998 Elsevier Science Ltd.All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00441-4