2-(benzo[d]thiazol-2-yl)phenyltrifluoromethanesulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-yl)phenyltrifluoromethanesulfonate
• 英文别名: [2-(1,3-Benzothiazol-2-yl)phenyl] trifluoromethanesulfonate；[2-(1,3-benzothiazol-2-yl)phenyl] trifluoromethanesulfonate
• 化学式: C₁₄H₈F₃NO₃S₂
• 分子量: 359.35
• InChiKey: BOOZMGFWWHMXNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-yl)phenyltrifluoromethanesulfonate 在 palladium diacetate 、 sodium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 16.67h， 生成
  参考文献：
  名称：

  Visualizing Peroxynitrite Fluxes in Endothelial Cells Reveals the Dynamic Progression of Brain Vascular Injury

  摘要：

  Accumulating evidence suggests that formation of peroxynitrite (ONOO-) in the cerebral vasculature contributes to the progression of ischemic damage, while the underlying molecular mechanisms remain elusive. To fully understand ONOO- biology, efficient tools that can realize the real-time tracing of endogenous ONOO- fluxes are indispensable. While a few ONOO- fluorescent probes have been reported, direct visualization of ONOO- fluxes in the cerebral vasculature of live mice remains a challenge. Herein, we present a fluorescent switch-on probe (NP3) for ONOO- imaging. NP3 exhibits good specificity, fast response, and high sensitivity toward ONOO- both in vitro and in vivo. Moreover, NP3 is two-photon excitable and readily blood-brain barrier penetrable. These desired photophysical and pharmacokinetic properties endow NP3 with the capability to monitor brain vascular ONOO- generation after injury with excellent temporal and spatial resolution. As a proof of concept, NP3 has enabled the direct visualization of neurovascular ONOO- formation in ischemia progression in live mouse brain by use of two-photon laser scanning microscopy. Due to these favorable properties, NP3 holds great promise for visualizing endogenous peroxynitrite fluxes in a variety of pathophysiological progressions in vitro and in vivo.

  DOI：

  10.1021/jacs.5b06865
• 作为产物：
  描述：

  2-氨基苯硫醇 在 吡啶 、 盐酸 、 双氧水 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2-(benzo[d]thiazol-2-yl)phenyltrifluoromethanesulfonate
  参考文献：
  名称：

  检测过氧化亚硝基的荧光探针及制备和应用

  摘要：

  本发明提供一类检测过氧化亚硝基的荧光探针，具有式Ia或Ib的结构通式，通过（1）R4取代的邻氨基苯硫酚或者R4取代的邻氨基苯酚与R1、R2取代的苯甲醛在甲醇溶液中室温搅拌两个小时，得1a；（2）R4取代的邻氨基苯硫酚或者邻氨基苯酚与R2取代的邻羟基苯甲醛进行氧化缩合，得苯并噻唑类或苯并恶唑类中间体；该中间体的酚羟基转化为三氟甲磺酸酯后与R3取代的对羟基苯叔丁基二甲基硅醚或对氨基苯叔丁基二甲基硅醚偶联，经苯胺氮原子甲基化、羟基脱除硅醚保护基，得Ib。本发明提供的荧光探针可与过氧化亚硝基特异性快速反应，生成具有强荧光的产物，从而实现对过氧化亚硝基的特异性检测。本发明探针的结构通式：。

  公开号：

  CN104893711B

文献信息

• [EN] BENZOTHIAZOLE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE<br/>[FR] INHIBITEURS BENZOTHIAZOLE DE LA POLY(ADP-RIBOSE)POLYMÉRASE
  申请人：ABBOTT LAB

  公开号：WO2010083199A1

  公开（公告）日：2010-07-22

  Inhibitors of poly(ADP-ribose)polymerase having a structure of Formula (I), ways to make them and methods of treating patients using them are disclosed.
• Visualizing Peroxynitrite Fluxes in Endothelial Cells Reveals the Dynamic Progression of Brain Vascular Injury
  作者：Xin Li、Rong-Rong Tao、Ling-Juan Hong、Juan Cheng、Quan Jiang、Ying-Mei Lu、Mei-Hua Liao、Wei-Feng Ye、Nan-Nan Lu、Feng Han、Yong-Zhou Hu、You-Hong Hu

  DOI：10.1021/jacs.5b06865

  日期：2015.9.30

  Accumulating evidence suggests that formation of peroxynitrite (ONOO-) in the cerebral vasculature contributes to the progression of ischemic damage, while the underlying molecular mechanisms remain elusive. To fully understand ONOO- biology, efficient tools that can realize the real-time tracing of endogenous ONOO- fluxes are indispensable. While a few ONOO- fluorescent probes have been reported, direct visualization of ONOO- fluxes in the cerebral vasculature of live mice remains a challenge. Herein, we present a fluorescent switch-on probe (NP3) for ONOO- imaging. NP3 exhibits good specificity, fast response, and high sensitivity toward ONOO- both in vitro and in vivo. Moreover, NP3 is two-photon excitable and readily blood-brain barrier penetrable. These desired photophysical and pharmacokinetic properties endow NP3 with the capability to monitor brain vascular ONOO- generation after injury with excellent temporal and spatial resolution. As a proof of concept, NP3 has enabled the direct visualization of neurovascular ONOO- formation in ischemia progression in live mouse brain by use of two-photon laser scanning microscopy. Due to these favorable properties, NP3 holds great promise for visualizing endogenous peroxynitrite fluxes in a variety of pathophysiological progressions in vitro and in vivo.
• 检测过氧化亚硝基的荧光探针及制备和应用
  申请人：浙江大学

  公开号：CN104893711B

  公开（公告）日：2017-04-05

  本发明提供一类检测过氧化亚硝基的荧光探针，具有式Ia或Ib的结构通式，通过（1）R4取代的邻氨基苯硫酚或者R4取代的邻氨基苯酚与R1、R2取代的苯甲醛在甲醇溶液中室温搅拌两个小时，得1a；（2）R4取代的邻氨基苯硫酚或者邻氨基苯酚与R2取代的邻羟基苯甲醛进行氧化缩合，得苯并噻唑类或苯并恶唑类中间体；该中间体的酚羟基转化为三氟甲磺酸酯后与R3取代的对羟基苯叔丁基二甲基硅醚或对氨基苯叔丁基二甲基硅醚偶联，经苯胺氮原子甲基化、羟基脱除硅醚保护基，得Ib。本发明提供的荧光探针可与过氧化亚硝基特异性快速反应，生成具有强荧光的产物，从而实现对过氧化亚硝基的特异性检测。本发明探针的结构通式：。