(4-((1-((3S,5S)-5-(bis(ethylthio)methyl)-1-(4-(5-(4-((4-((S)-2-(bis(ethylthio)methyl)pyrrolidine-1-carbonyl)-2-methoxy-5-nitro-phenoxy)methyl)-1H-1,2,3-triazol-1-yl)pentyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)-5-methoxy-2-nitrophenyl)((S)-2-(bis(ethylthio)methyl)pyrrolidin-1-yl)methanone | 1238824-62-8

• 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: (4-((1-((3S,5S)-5-(bis(ethylthio)methyl)-1-(4-(5-(4-((4-((S)-2-(bis(ethylthio)methyl)pyrrolidine-1-carbonyl)-2-methoxy-5-nitro-phenoxy)methyl)-1H-1,2,3-triazol-1-yl)pentyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)-5-methoxy-2-nitrophenyl)((S)-2-(bis(ethylthio)methyl)pyrrolidin-1-yl)methanone
• 英文别名: [4-[[1-[5-[4-[(2S,4S)-2-[bis(ethylsulfanyl)methyl]-4-[4-[[4-[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]methyl]triazol-1-yl]pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]pentyl]triazol-4-yl]methoxy]-5-methoxy-2-nitrophenyl]-[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidin-1-yl]methanone
• CAS: 1238824-62-8
• 化学式: C₆₂H₈₄N₁₂O₁₅S₆
• 分子量: 1429.82
• InChiKey: VQCQMRZRTWAYLC-KHBHYRCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.19
• 重原子数：
  95.0
• 可旋转键数：
  38.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  307.15
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  (4-((1-((3S,5S)-5-(bis(ethylthio)methyl)-1-(4-(5-(4-((4-((S)-2-(bis(ethylthio)methyl)pyrrolidine-1-carbonyl)-2-methoxy-5-nitro-phenoxy)methyl)-1H-1,2,3-triazol-1-yl)pentyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)-5-methoxy-2-nitrophenyl)((S)-2-(bis(ethylthio)methyl)pyrrolidin-1-yl)methanone 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成
  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
• 作为产物：
  描述：

  (2S)-N-[5-methoxy-4-(2-propynyloxy)-2-nitrobenzoyl]-pyrrolidine-2-carboxaldehyde diethyl-dithioacetal 、 ((2S,4S)-4-azido-2-(bis(ethylthio)methyl)pyrrolidin-1-yl)(4-(5-azidopentyloxy)-5-methoxy-2-nitrophenyl)methanone 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以88%的产率得到(4-((1-((3S,5S)-5-(bis(ethylthio)methyl)-1-(4-(5-(4-((4-((S)-2-(bis(ethylthio)methyl)pyrrolidine-1-carbonyl)-2-methoxy-5-nitro-phenoxy)methyl)-1H-1,2,3-triazol-1-yl)pentyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)-5-methoxy-2-nitrophenyl)((S)-2-(bis(ethylthio)methyl)pyrrolidin-1-yl)methanone
  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.