[5,6]-benz-1-aza-cyclodec-3,7-diyne | 457071-54-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [5,6]-benz-1-aza-cyclodec-3,7-diyne
• 英文别名: 5-Azabicyclo[8.4.0]tetradeca-1(14),10,12-trien-2,8-diyne
• CAS: 457071-54-4
• 化学式: C₁₃H₁₁N
• 分子量: 181.237
• InChiKey: YQTGDDMDGVOTAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [5,6]-benz-1-aza-cyclodec-3,7-diyne 在 dirhodium tetraacetate 对甲苯磺酰叠氮 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (4R,5S)-6-Oxo-7-aza-tricyclo[10.4.0.0^4,7]hexadeca-1(16),12,14-triene-2,10-diyne-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  A carbene insertion route to β-lactam fused cyclic enediynes

  摘要：

  A new methodology has been developed for the synthesis of biologically important beta-lactam fused enediynes 1 and 2. The key step is the successful insertion of the carbene generated from the diazo enediynes 3 and 4. The result is in sharp contrast to the fate of the carbene generated from acyclic enediyne 5 in which case the rearrangement product 6 and the dimer 7 were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00724-4
• 作为产物：
  描述：

  methanesulfonic acid 4-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenyl}-but-3-ynyl ester 在 sodium azide 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 苯硫酚 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [5,6]-benz-1-aza-cyclodec-3,7-diyne
  参考文献：
  名称：

  Benzene fused monocyclic enediynyl amides: synthesis, reactivity and DNA-Cleavage activity in comparison to the corresponding sulfonamides

  摘要：

  Monocyclic enediynyl amides 2a 2c have been synthesized via the corresponding free amine 5. Kinetic studies in chloroform revealed the reactivity of these amides towards Bergman cyclization to be less than that of the corresponding sulfonamides. However, differential scanning calorimetry (DSC) measurements in the solid state and DNA-cleavage studies in aqueous buffer showed higher reactivity for the amides than the sulphonamides. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00029-x

文献信息

• Synthesis of highly efficient pH-sensitive DNA cleaving aminomethyl N-substituted cyclic enediyne and its L-lysine conjugate
  作者：Ishita Hatial、Partha S. Addy、Ananta K. Ghosh、Amit Basak

  DOI：10.1016/j.tetlet.2012.11.102

  日期：2013.2

  Two 10-membered benzo-fused N-substituted cyclic enediynes, one an amino methyl and the other, a C-lysine conjugated derivative 2 and 3, respectively were synthesized (as a 1.2:1 mixture of regioisomers) and their DNA-cleavage efficiency studied. Both the compounds showed much better DNA-cleavage profile than that of the parent unsubstituted enediyne 1. The lysine conjugate 3 showed an efficient pH

  分别合成了两个10元苯并稠合的N-取代的环状烯二炔，一个为氨基甲基，另一个为C-赖氨酸共轭衍生物2和3（作为区域异构体的1.2：1混合物）及其DNA裂解效率。研究过。与母体未取代的二烯1相比，这两种化合物都显示出更好的DNA裂解特性。在环境条件下，赖氨酸结合物3表现出有效的pH依赖性裂解，达到线性DNA形成的〜50％。
• Trienediynes on a 1,3,5-trisubstituted benzene template: a new approach for enhancement of reactivity
  作者：Ishita Hatial、Saibal Jana、Shrabani Bisai、Manasmita Das、Ananta Kumar Ghosh、Anakuthil Anoop、Amit Basak

  DOI：10.1039/c4ra04794j

  日期：——

  The synthesis of trienediynes based on a 1,3,5-trisubstituted benzene template is described. The presence of three adjacent enediyne moieties in the dendritic core exerted a cooperative effect to bring down the onset temperature for Bergman cyclization leading to increased DNA cleavage in a shorter time.

  本文介绍了以 1,3,5-三取代苯为模板合成三烯二炔的方法。树枝状核心中三个相邻烯二炔分子的存在产生了协同效应，降低了伯格曼环化的起始温度，从而在更短的时间内提高了 DNA 的裂解率。
• Design and synthesis of enediyne–peptide conjugates and their inhibiting activity against chymotrypsin
  作者：Sansa Dutta、Amit Basak、Swagata Dasgupta

  DOI：10.1016/j.bmc.2009.04.019

  日期：2009.6

  Novel enediyne-amino acid conjugates 1-4 have been synthesized. All of these effectively target the enzyme chymotrypsin inhibiting its proteolytic activity. The conjugate with a directly linked phenyl alanine is the most effective inhibitor with a K-i of 3 mu M. The mode of inhibition is mostly competitive or of a mixed type depending on the nature of the inhibitor. (C) 2009 Elsevier Ltd. All rights reserved.
• Benzofused N-substituted cyclic enediynes: Activation and DNA-cleavage potential
  作者：Amit Basak、Moumita Kar

  DOI：10.1016/j.bmc.2008.02.044

  日期：2008.4

  The effect of electron withdrawal on the reactivity of N-substituted cyclic enediynes has been studied. These were synthesized via an intramolecular Mitsunobu reaction. The electron withdrawing effect of the nitro groups or the positive charge on the free ammonium salts was found to lower the cyclization temperature for Bergman cyclization. The ammonium salts cleave ds-DNA at nanomolar concentrations. (c) 2008 Published by Elsevier Ltd.
• Benzene fused monocyclic enediynyl amides: synthesis, reactivity and DNA-Cleavage activity in comparison to the corresponding sulfonamides
  作者：Amit Basak、Subrata Mandal、Amit Kumar Das、Valerio Bertolasi

  DOI：10.1016/s0960-894x(02)00029-x

  日期：2002.3

  Monocyclic enediynyl amides 2a 2c have been synthesized via the corresponding free amine 5. Kinetic studies in chloroform revealed the reactivity of these amides towards Bergman cyclization to be less than that of the corresponding sulfonamides. However, differential scanning calorimetry (DSC) measurements in the solid state and DNA-cleavage studies in aqueous buffer showed higher reactivity for the amides than the sulphonamides. (C) 2002 Published by Elsevier Science Ltd.