N-(3-methoxycarbonylphenoxy)phthalimide | 849048-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3-methoxycarbonylphenoxy)phthalimide
• 英文别名: methyl 3-(1,3-dioxoisoindol-2-yl)oxybenzoate
• CAS: 849048-58-4
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: HQJBAILFFBZYDF-UHFFFAOYSA-N

物化性质

• 沸点：
  461.2±47.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-methoxycarbonylphenoxy)phthalimide 在 lithium hydroxide 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 36.0h， 生成 O-(3-carboxyphenyl)hydroxylamine
  参考文献：
  名称：

  Bisaryloxime Ethers as Potent Inhibitors of Transthyretin Amyloid Fibril Formation

  摘要：

  Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.

  DOI：

  10.1021/jm049274d
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 3-甲氧基羰基苯硼酸 在 吡啶 、 copper(l) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 N-(3-methoxycarbonylphenoxy)phthalimide
  参考文献：
  名称：

  电化学硒催化 N-芳氧基酰胺的对氨基化：获得多取代的氨基酚

  摘要：

  氨基酚是一类重要的化合物，具有抗癌、抗炎、抗疟、抗菌等多种药理活性。在此，我们介绍了一种温和有效的电化学硒催化策略来合成多取代氨基酚。高原子效率和无过渡金属和无氧化剂条件是该协议的显着特征。通过合并电化学和有机硒催化过程， N-芳氧基酰胺的分子内重排在室温下在简单的不可分割的电池中产生对氨基化产物。

  DOI：

  10.1039/d3ob01116j

文献信息

• Inhibitors of transthyretin amyloid fibril formation
  申请人：Kelly W. Jeffery

  公开号：US20060178527A1

  公开（公告）日：2006-08-10

  Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.

  Bisaryloxime醚和bisarylhydroazones被证明对抑制甲状腺前蛋白淀粉样纤维的形成有效。
• Inhibitors of Transthyretin Amyloid Fibril Formation
  申请人：Kelly Jeffery W.

  公开号：US20090054629A1

  公开（公告）日：2009-02-26

  Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.

  Bisaryloxime醚和bisarylhydroazones已被证明对抑制转甲状腺原蛋白淀粉样纤维的形成具有有效性。
• US7312361B2
  申请人：——

  公开号：US7312361B2

  公开（公告）日：2007-12-25
• Bisaryloxime Ethers as Potent Inhibitors of Transthyretin Amyloid Fibril Formation
  作者：Steven M. Johnson、H. Michael Petrassi、Satheesh K. Palaninathan、Nilofar N. Mohamedmohaideen、Hans E. Purkey、Christopher Nichols、Kyle P. Chiang、Traci Walkup、James C. Sacchettini、K. Barry Sharpless、Jeffery W. Kelly

  DOI：10.1021/jm049274d

  日期：2005.3.1

  Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.
• Electrochemical selenium-catalyzed <i>para</i>-amination of <i>N</i>-aryloxyamides: access to polysubstituted aminophenols
  作者：Lei Gao、Zhi-Feng Wang、Lin-Wei Wang、Hai-Tao Tang、Zu-Yu Mo、Mu-Xue He

  DOI：10.1039/d3ob01116j

  日期：——

  Aminophenols are a class of important compounds with various pharmacological activities such as anticancer, anti-inflammatory, antimalarial, and antibacterial activities. Herein, we introduce a mild and efficient electrochemical selenium-catalyzed strategy to synthesize polysubstituted aminophenols. High atom efficiency and transition metal-free and oxidant-free conditions are the striking features

  氨基酚是一类重要的化合物，具有抗癌、抗炎、抗疟、抗菌等多种药理活性。在此，我们介绍了一种温和有效的电化学硒催化策略来合成多取代氨基酚。高原子效率和无过渡金属和无氧化剂条件是该协议的显着特征。通过合并电化学和有机硒催化过程， N-芳氧基酰胺的分子内重排在室温下在简单的不可分割的电池中产生对氨基化产物。