N-(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)succinamic acid pentafluorophenyl ester | 1269638-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: N-(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)succinamic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 4-[2-[2-[2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]ethoxy]ethoxy]ethylamino]-4-oxobutanoate；(2,3,4,5,6-pentafluorophenyl) 4-[2-[2-[2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]ethoxy]ethoxy]ethylamino]-4-oxobutanoate
• CAS: 1269638-08-5
• 化学式: C₂₂H₂₀F₅N₅O₈
• 分子量: 577.422
• InChiKey: DTCUTYNRTHPXPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)succinamic acid pentafluorophenyl ester 在 silica gel 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以100%的产率得到1-[2-[2-[2-[(4-Nitro-2,1,3-benzoxadiazol-7-yl)amino]ethoxy]ethoxy]ethyl]pyrrolidine-2,5-dione
  参考文献：
  名称：

  Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold

  摘要：

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.

  DOI：

  10.1021/ol1028173
• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 caesium carbonate 、 sodium sulfate 、 N,N-二异丙基乙胺 、 三氟乙酸 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 10.5h， 生成 N-(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)succinamic acid pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold

  摘要：

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.

  DOI：

  10.1021/ol1028173

文献信息

• Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold
  作者：Sabrina Noël、Laurent Guillon、Isabelle J. Schalk、Gaëtan L. A. Mislin

  DOI：10.1021/ol1028173

  日期：2011.3.4

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.