phenanthridinone N-acetic acid | 37046-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: phenanthridinone N-acetic acid
• 英文别名: (6-oxo-6H-phenanthridin-5-yl)acetic acid；(6-Oxo-6H-phenanthridin-5-yl)-acetic acid；2-(6-oxophenanthridin-5-yl)acetic acid
• CAS: 37046-34-7
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: MWCWZXJYYOFOAS-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C
• 沸点：
  523.2±42.0 °C(predicted)
• 密度：
  1.362±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenanthridinone N-acetic acid 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 生成 2-thioxo-2,3-dihydro-thiazolo[3,2-f]phenanthridinylium betaine
  参考文献：
  名称：

  anhydro-2-Mercaptothiazolo[3,2-f]phenanthridinium hydroxide, a mesoionic thiazole ring system containing exocyclic sulfur

  摘要：

  DOI：

  10.1021/jo00434a046
• 作为产物：
  描述：

  菲啶 在 sodium hydroxide 、 双氧水 、 乙酸酐 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 41.0h， 生成 phenanthridinone N-acetic acid
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017

文献信息

• Palladium‐Catalyzed Intramolecular Decarboxylative Coupling of Arene Carboxylic Acids/Esters with Aryl Bromides
  作者：Zengming Shen、Zhenjie Ni、Song Mo、Jing Wang、Yamin Zhu

  DOI：10.1002/chem.201103438

  日期：2012.4.16

  Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad.

  给我一个戒指？已经开发出一种有效的方法用于芳烃羧酸/酯与钯催化的芳基溴化物的分子内脱羧偶联（参见方案）。从合成的观点来看，该方法极具吸引力，因为催化剂的负载量低，优化的反应条件温和且底物范围广。
• ORGANIC METAL COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE
  申请人：INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE

  公开号：US20210179649A1

  公开（公告）日：2021-06-17

  Organic metal compounds, and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I): The definitions of R 1 -R 18 and n are as defined in specification. The organic light-emitting device includes a pair of electrodes; and an organic light-emitting element, disposed between the electrodes, wherein the organic light-emitting element includes the aforementioned organic metal compound.

  提供有机金属化合物以及采用这些金属化合物的有机发光器件。有机金属化合物具有化学结构式（I）的化学结构：R1-R18和n的定义如规范中所定义。有机发光器件包括一对电极；以及放置在电极之间的有机发光元件，其中有机发光元件包括上述有机金属化合物。
• POTTS K. T.; YAO S., J. ORG. CHEM., 1979, 44, NO 6, 977-979
  作者：POTTS K. T.、 YAO S.

  DOI：——

  日期：——
• J. MED. CHEM., 32,(1989) N, C. 1033-1038
  作者：

  DOI：——

  日期：——
• Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety
  作者：Jack DeRuiter、Blake E. Swearingen、Vinay Wandrekar、Charles A. Mayfield

  DOI：10.1021/jm00125a017

  日期：1989.5

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.