(2S,11aS)-7-methoxy-2-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-8-(4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one | 1238824-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: (2S,11aS)-7-methoxy-2-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-8-(4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one
• 英文别名: (6aS,8S)-8-[4-[[(6aS)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxymethyl]triazol-1-yl]-3-[4-[4-[[(6aS)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxymethyl]triazol-1-yl]butoxy]-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• CAS: 1238824-76-4
• 化学式: C₄₉H₅₂N₁₂O₉
• 分子量: 953.027
• InChiKey: HYABNVWFWJQKMS-CUPIEXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  70
• 可旋转键数：
  16
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  215
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以35 mg的产率得到(2S,11aS)-7-methoxy-2-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-8-(4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one
  参考文献：
  名称：

  Synthesis of bis-1,2,3-triazolo-bridged unsymmetrical pyrrolobenzodiazepine trimers via ‘click’ chemistry and their DNA-binding studies

  摘要：

  New conceivable synthetic approach for the construction of nitrogen-rich 1,2,3-triazolo-pyrrolo[2,1-c] [1,4]benzodiazepine (TPBD, 3a-c) trimers has been developed. The first example of a bis-1,2,3-triazolo-bridged unsymmetrical PBD trimer has been successfully synthesized by employing a CuAAC type 'click' chemistry protocol. This efficient route generates tri-imine functionality in a single molecule. It has been envisaged that such tri-imine functionalities could bring in efficient interaction with DNA in a sequence-selective manner in the minor groove of duplex DNA. One of the representative analogues 3c has shown improved DNA-binding ability (Delta T(m) 23.7 degrees C) by thermal denaturation studies using CT-DNA and this data is also supported by molecular modeling (MD) studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.003

文献信息

• Synthesis of bis-1,2,3-triazolo-bridged unsymmetrical pyrrolobenzodiazepine trimers via ‘click’ chemistry and their DNA-binding studies
  作者：Ahmed Kamal、Nagula Shankaraiah、Ch. Ratna Reddy、S. Prabhakar、Nagula Markandeya、Hemant Kumar Srivastava、G. Narahari Sastry

  DOI：10.1016/j.tet.2010.05.003

  日期：2010.7

  New conceivable synthetic approach for the construction of nitrogen-rich 1,2,3-triazolo-pyrrolo[2,1-c] [1,4]benzodiazepine (TPBD, 3a-c) trimers has been developed. The first example of a bis-1,2,3-triazolo-bridged unsymmetrical PBD trimer has been successfully synthesized by employing a CuAAC type 'click' chemistry protocol. This efficient route generates tri-imine functionality in a single molecule. It has been envisaged that such tri-imine functionalities could bring in efficient interaction with DNA in a sequence-selective manner in the minor groove of duplex DNA. One of the representative analogues 3c has shown improved DNA-binding ability (Delta T(m) 23.7 degrees C) by thermal denaturation studies using CT-DNA and this data is also supported by molecular modeling (MD) studies. (C) 2010 Elsevier Ltd. All rights reserved.