1-(2-nitrobenzenesulfonyl)amino-7-aminoheptane | 211512-14-0

• 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: 1-(2-nitrobenzenesulfonyl)amino-7-aminoheptane
• 英文别名: N-(6-aminoheptyl)-2-nitrobenzenesulfonamide；N1-(2-nitrobenzenesulfonyl)-1,7-diaminoheptane；N-(7-aminoheptyl)-2-nitrobenzenesulfonamide
• CAS: 211512-14-0
• 化学式: C₁₃H₂₁N₃O₄S
• 分子量: 315.393
• InChiKey: CSUADSIFEIGQDC-UHFFFAOYSA-N

物化性质

• 沸点：
  488.1±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-nitrobenzenesulfonyl)amino-7-aminoheptane 在 potassium carbonate 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 N¹,N⁶,N¹³-tris(2-nitrobenzenesulfonyl)-1,13-diamino-6-azatridecane
  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：

  1,7-二氨基庚烷 、 邻硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-nitrobenzenesulfonyl)amino-7-aminoheptane
  参考文献：
  名称：

  3-取代的双环咪唑并[1,2- d ] [1,2,4]噻二唑和三环苯并[4,5]咪唑[1,2- d ] [1,2,4]噻二唑的合成

  摘要：

  通过前体[1,2,4] thiadiazol-3-（2 H）one衍生物的交换反应（可能为有用的稠合环[1,2,4]噻二唑支架（例如7a和10b）的通用合成路线）（例如，6和9）与适当取代的腈类（例如溴化氰或p温和的条件下对甲苯磺酰氰化物）进行说明。例如，所述三环3-溴- [1,2,4] THD衍生物（图7a）行小号Ñ氩置换与各种亲核试剂，其中包括胺，丙二酸酯和醇。同样，双环3-对甲苯磺酰基[1,2,4] THD（10b）用作与二胺反应的模板，并且将所得的取代的二胺（例如12a或12e）以线性方式进一步选择性地在N1和/或N2位置衍生化。如方案6所示，获得了3-甲基双环[1,2,4] THD（21）的X射线晶体结构，并确认了通过保护-烷基化-脱保护方案在N1位选择性甲基化。或者，由10b反应短暂聚合N1官能化衍生物还开发了具有适当取代的仲胺的共聚物。因此，有利地利用这些合成策略来获得各种多样化衍生的3-取代的稠环[1

  DOI：

  10.1021/jo0507486

文献信息

• Structure–Activity Relationship Studies of Argiotoxins: Selective and Potent Inhibitors of Ionotropic Glutamate Receptors
  作者：Mette H. Poulsen、Simon Lucas、Tinna B. Bach、Anne F. Barslund、Claudius Wenzler、Christel B. Jensen、Anders S. Kristensen、Kristian Strømgaard

  DOI：10.1021/jm301602d

  日期：2013.2.14

  open-channel blocker of ionotropic glutamate (iGlu) receptors. Here, three series of analogues were designed to exploit selectivity among iGlu receptors, taking advantage of a recently developed solid-phase synthetic methodology for the synthesis of ArgTX-636 and analogues. Initially, the importance of secondary amino groups in the polyamine chain was studied by the synthesis of systematically modified

  Argiotoxin-636（ArgTX-636），来自蜘蛛Argiope lobata的天然产物，是离子型谷氨酸（iGlu）受体的有效但非选择性的开放通道阻滞剂。在这里，设计了三个系列的类似物，以利用iGlu受体之间的选择性，利用最近开发的用于合成ArgTX-636和类似物的固相合成方法。最初，通过合成系统修饰的ArgTX-636类似物研究了多胺链中仲氨基的重要性，并对其在NMDA和AMPA受体上的药理活性进行了评估。这导致鉴定出分别优先于NMDA和AMPA受体的两种化合物。通过系统地改变芳族头基和连接基氨基酸，可以进一步修饰这些化合物，从而分别得到对NMDA和AMPA受体具有增强的效力和选择性的化合物。因此，
• US6191273B1
  申请人：——

  公开号：US6191273B1

  公开（公告）日：2001-02-20
• Synthesis of 3-Substituted Bicyclic Imidazo[1,2-<i>d</i>][1,2,4]thiadiazoles and Tricyclic Benzo[4,5]imidazo[1,2-<i>d</i>][1,2,4]thiadiazoles
  作者：Regis Leung-Toung、Tim F. Tam、Yanqing Zhao、Craig D. Simpson、Wanren Li、Denis Desilets、Khashayar Karimian

  DOI：10.1021/jo0507486

  日期：2005.8.1

  cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively

  通过前体[1,2,4] thiadiazol-3-（2 H）one衍生物的交换反应（可能为有用的稠合环[1,2,4]噻二唑支架（例如7a和10b）的通用合成路线）（例如，6和9）与适当取代的腈类（例如溴化氰或p温和的条件下对甲苯磺酰氰化物）进行说明。例如，所述三环3-溴- [1,2,4] THD衍生物（图7a）行小号Ñ氩置换与各种亲核试剂，其中包括胺，丙二酸酯和醇。同样，双环3-对甲苯磺酰基[1,2,4] THD（10b）用作与二胺反应的模板，并且将所得的取代的二胺（例如12a或12e）以线性方式进一步选择性地在N1和/或N2位置衍生化。如方案6所示，获得了3-甲基双环[1,2,4] THD（21）的X射线晶体结构，并确认了通过保护-烷基化-脱保护方案在N1位选择性甲基化。或者，由10b反应短暂聚合N1官能化衍生物还开发了具有适当取代的仲胺的共聚物。因此，有利地利用这些合成策略来获得各种多样化衍生的3-取代的稠环[1
• 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.