N¹,N³,N⁶-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane | 211512-11-7

• 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: N¹,N³,N⁶-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane
• 英文别名: 2-nitro-N-[3-[(2-nitrophenyl)sulfonyl-[2-[(2-nitrophenyl)sulfonylamino]ethyl]amino]propyl]benzenesulfonamide
• CAS: 211512-11-7
• 化学式: C₂₃H₂₄N₆O₁₂S₃
• 分子量: 672.675
• InChiKey: UEVCQFPOJXJSMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  292
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N¹,N³,N⁶-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane 在 Tesser's base 、 sodium thiophenolate 、 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3,6,10-Tris-(3-tert-butoxycarbonylamino-propyl)-3,6,10-triaza-bicyclo[10.3.1]hexadeca-1(16),12,14-triene-14-carboxylic acid
  参考文献：
  名称：

  受仿生万古霉素启发的生物合成受体分子。

  摘要：

  制备了具有三氮杂环烷骨架的具有生物启发性的合成受体分子的512个成员的文库。该支架的目的是定位三个（相同的）肽“结合臂”，以模仿万古霉素抗生素中存在的抗生素结合腔。用含有D-Ala-D-Ala和D-Ala-D-Lac的配体筛选文库，这些配体存在于致病细菌的细胞壁前体中。筛选和验证导致鉴定出能够结合这些配体的合成受体。

  DOI：

  10.1016/s0960-894x(01)00237-2
• 作为产物：
  描述：

  N-(2-乙氨基)-1,3-丙二胺 、 邻硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到N¹,N³,N⁶-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane
  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

文献信息

• Synthesis of polyazacyclophane-intercalator conjugates for combinatorial chemistry and RNA interaction studies
  作者：Tingmin Wang、Haoyun An、Becky D. Haly、P. Dan Cook

  DOI：10.1002/jhet.5570370403

  日期：2000.7

  were conjugated to different positions of several polyaza-pyridinocyclophanes by various linkers to provide thirteen new polyazacyclophane-intercalator conjugates 1–13. These resulting conjugates contain two or three constrained secondary nitrogen atoms on the ring, which may serve as nucleophilic, coordinating or hydrogen-bonding sites for combinatorial, RNA interaction and coordination studies.

  蒽醌和pyr嵌入剂通过各种连接剂偶联到几个聚氮杂-吡啶酮环烷的不同位置上，从而提供了13种新的聚氮杂环烷-嵌入剂偶联物1-13。这些所得的缀合物在环上包含两个或三个受约束的仲氮原子，这些氮原子可作为亲核，配位或氢键结合位点，用于组合，RNA相互作用和配位研究。
• New piperazinyl polyazacyclophane scaffolds, libraries and biological activities
  作者：Haoyun An、Becky D. Haly、P.Dan Cook

  DOI：10.1016/s0960-894x(98)00424-7

  日期：1998.9

  Four novel unsymmetric piperazinyl polyazacyclophane scaffolds 1-4 were synthesized in high yields by an efficient cyclization strategy. Twenty-six libraries 12-37 (total 16000 compounds) were generated by a solution-phase combinatorial approach from 1-4 and thirty-eight functional groups. Potent antibacterial and HIV-1 tat/TAR protein-RNA disrupting activities were discovered. (C) 1998 Elsevier Science Ltd. All rights reserved.
• US6191273B1
  申请人：——

  公开号：US6191273B1

  公开（公告）日：2001-02-20
• Synthesis of novel polyazadipyridinocyclophane scaffolds and their application for the generation of libraries
  作者：Tingmin Wang、Haoyun An、Timothy A. Vickers、Ramesh Bharadwaj、P.Dan Cook

  DOI：10.1016/s0040-4020(98)00441-4

  日期：1998.7

  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.
• Bio-inspired synthetic receptor molecules towards mimicry of vancomycin
  作者：Menno C.F Monnee、Arwin J Brouwer、Linda M Verbeek、André M.A van Wageningen、Rob M.J Liskamp

  DOI：10.1016/s0960-894x(01)00237-2

  日期：2001.6

  A 512-member library of bio-inspired synthetic receptor molecules was prepared featuring a triazacyclophane scaffold. The purpose of this scaffold was to orient three (identical) peptide 'binding arms' in order to mimic an antibiotic binding cavity as is present in the vancomycin antibiotics. The library was screened with D-Ala-D-Ala and D-Ala-D-Lac containing ligands, which are present in the cell

  制备了具有三氮杂环烷骨架的具有生物启发性的合成受体分子的512个成员的文库。该支架的目的是定位三个（相同的）肽“结合臂”，以模仿万古霉素抗生素中存在的抗生素结合腔。用含有D-Ala-D-Ala和D-Ala-D-Lac的配体筛选文库，这些配体存在于致病细菌的细胞壁前体中。筛选和验证导致鉴定出能够结合这些配体的合成受体。