6-amino-7-(3-hydroxyphenoxy)-4-methyl-2H-chromen-2-one | 1398947-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-amino-7-(3-hydroxyphenoxy)-4-methyl-2H-chromen-2-one
• 英文别名: PN600；6-Amino-7-(3-hydroxyphenoxy)-4-methylchromen-2-one；6-amino-7-(3-hydroxyphenoxy)-4-methylchromen-2-one
• CAS: 1398947-59-5
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: KCEYVYVZDSSXCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-7-(3-hydroxyphenoxy)-4-methyl-2H-chromen-2-one 在 次氯酸离子 作用下， 以 aq. phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-氨基-7-羟基-4-甲基香豆素
  参考文献：
  名称：

  Understanding the Selectivity of a Multichannel Fluorescent Probe for Peroxynitrite Over Hypochlorite

  摘要：

  过氧亚硝酸盐是一种显著的生物活性氮物种，源自一氧化氮和超氧化物的自由基结合，并根本参与广泛的生理和病理过程。虽然本身不具氧化还原惰性，但过氧亚硝酸盐阴离子（OONO–）攻击各种生物亲电体，生成一系列强效的2-电子或1-电子氧化剂，导致细胞损伤。开发不受次氯酸盐干扰的过氧亚硝酸盐荧光探针，一直是化学界的热门课题。我们此前报道了一种过氧亚硝酸盐探针（PN600），该探针通过多通道信号机制能区分次氯酸盐和过氧亚硝酸盐。在此，通过结构-反应性关系研究，解释了这种有趣的特异性。此外，这项工作结合丰富的文献贡献，提供了一个定性指导原则，即利用富电子芳香族基团设计针对过氧亚硝酸盐和/或次氯酸盐的探针。通过开发另一系列选择性过氧亚硝酸盐探针，进一步验证了该指导原则的可行性。

  DOI：

  10.1021/acs.bioconjchem.5b00396
• 作为产物：
  描述：

  7-fluoro-4-methyl-6-nitro-2H-chromen-2-one 在 5%-palladium/activated carbon 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， -78.0~85.0 ℃ 、413.7 kPa 条件下， 反应 24.0h， 生成 6-amino-7-(3-hydroxyphenoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  A Three-Channel Fluorescent Probe That Distinguishes Peroxynitrite from Hypochlorite

  摘要：

  A novel fluorescent probe for peroxynitrite, PN600, was rationally designed on the basis of a unique fluorophore assembly approach. PN600 is a green-emitting coumarin derivative. Upon oxidation by peroxynitrite, PN600 is transformed into a highly fluorescent red-emitting resorufin derivative via an orange-emitting intermediate. This three-channel signaling capability enables PN600 to differentiate peroxynitrite from other reactive oxygen and nitrogen species, including hypochlorite and hydroxyl radical. Moreover, PN600 is membrane permeable and compatible with common TRITC filter sets and displays low cytotoxicity. Therefore, PN600 is a promising candidate for in vitro peroxynitrite imaging.

  DOI：

  10.1021/ja305046u

文献信息

• Understanding the Selectivity of a Multichannel Fluorescent Probe for Peroxynitrite Over Hypochlorite
  作者：Quanjuan Zhang、Na Zhang、Yi-Tao Long、Xuhong Qian、Youjun Yang

  DOI：10.1021/acs.bioconjchem.5b00396

  日期：2016.2.17

  Peroxynitrite is a prominent biological reactive nitrogen species from radical combination of nitric oxide and superoxide and fundamentally involved in broad spectrum physiological and pathological processes. Though redox-inert itself, peroxynitrite anion (OONO–) attacks various biological electrophiles to generate an array of potent 2-e– or 1-e– oxidants, which result in cell injuries. Development of fluorescent probes for peroxynitrite, free from interference from hypochlorite, has been an active endeavor of the chemical community. We previously reported a peroxynitrite probe (PN600), which could differentiate hypochlorite from peroxynitrite through a multichannel signaling mechanism. Herein, this intriguing selectivity was accounted for through a structure–reactivity relationship study. Also, this work, together with rich literature contributions, has allowed a qualitative guideline in the use of electron-rich aromatic moieties to design probes against peroxynitrite and/or hypochlorite. The viability of this guideline was further testified by development of another list of peroxynitrite selective probes.

  过氧亚硝酸盐是一种显著的生物活性氮物种，源自一氧化氮和超氧化物的自由基结合，并根本参与广泛的生理和病理过程。虽然本身不具氧化还原惰性，但过氧亚硝酸盐阴离子（OONO–）攻击各种生物亲电体，生成一系列强效的2-电子或1-电子氧化剂，导致细胞损伤。开发不受次氯酸盐干扰的过氧亚硝酸盐荧光探针，一直是化学界的热门课题。我们此前报道了一种过氧亚硝酸盐探针（PN600），该探针通过多通道信号机制能区分次氯酸盐和过氧亚硝酸盐。在此，通过结构-反应性关系研究，解释了这种有趣的特异性。此外，这项工作结合丰富的文献贡献，提供了一个定性指导原则，即利用富电子芳香族基团设计针对过氧亚硝酸盐和/或次氯酸盐的探针。通过开发另一系列选择性过氧亚硝酸盐探针，进一步验证了该指导原则的可行性。
• A Three-Channel Fluorescent Probe That Distinguishes Peroxynitrite from Hypochlorite
  作者：Quanjuan Zhang、Zhichuan Zhu、Yongli Zheng、Jiagao Cheng、Na Zhang、Yi-Tao Long、Jing Zheng、Xuhong Qian、Youjun Yang

  DOI：10.1021/ja305046u

  日期：2012.11.14

  A novel fluorescent probe for peroxynitrite, PN600, was rationally designed on the basis of a unique fluorophore assembly approach. PN600 is a green-emitting coumarin derivative. Upon oxidation by peroxynitrite, PN600 is transformed into a highly fluorescent red-emitting resorufin derivative via an orange-emitting intermediate. This three-channel signaling capability enables PN600 to differentiate peroxynitrite from other reactive oxygen and nitrogen species, including hypochlorite and hydroxyl radical. Moreover, PN600 is membrane permeable and compatible with common TRITC filter sets and displays low cytotoxicity. Therefore, PN600 is a promising candidate for in vitro peroxynitrite imaging.