2-(2-oxobenzo[cd]indol-1(2H)-yl)acetic acid | 39273-46-6

• 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: 2-(2-oxobenzo[cd]indol-1(2H)-yl)acetic acid
• 英文别名: (2-oxo-2H-benzo[cd]indol-1-yl)-acetic acid；(2-oxo-1,2-dihydro-benz[cd]indol-1-yl)-acetic acid；(2-Oxo-1,2-dihydro-benz[cd]indol-1-yl)-essigsaeure；Naphthostyryl-N-essigsaeure；(2-oxobenzo[cd]indol-1(2H)-yl)acetic acid；2-(2-oxobenzo[cd]indol-1-yl)acetic acid
• CAS: 39273-46-6
• 化学式: C₁₃H₉NO₃
• mdl: MFCD00522142
• 分子量: 227.219
• InChiKey: CXOJEFXQICMXBG-UHFFFAOYSA-N

物化性质

• 熔点：
  250-252 °C
• 沸点：
  509.3±42.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(2-oxobenzo[cd]indol-1(2H)-yl)acetic acid 、 氯 生成 2,4-Dichlornaphthostyril-N-essigsaeure
  参考文献：
  名称：

  KARISHIN, A. P.;DANILYUK, T. P.;PECHKA, A. A.;TITARENKO, V. P.;GRINEVA, N+, 12-J MENDELEEVSK. SEZD PO OBSHCH. I PRIKL. XIMII. REF. DOKL. I SOOBSHCH.6+

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-oxo-1,2-dihydro-benz[cd]indol-1-yl)-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-(2-oxobenzo[cd]indol-1(2H)-yl)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

• Small Molecule–Peptide Conjugates as Dimerization Inhibitors of Leishmania infantum Trypanothione Disulfide Reductase
  作者：Alejandro Revuelto、Isabel López-Martín、Héctor de Lucio、Juan Carlos García-Soriano、Nicola Zanda、Sonia de Castro、Federico Gago、Antonio Jiménez-Ruiz、Sonsoles Velázquez、María-José Camarasa

  DOI：10.3390/ph14070689

  日期：——

  Trypanothione disulfide reductase (TryR) is an essential homodimeric enzyme of trypanosomatid parasites that has been validated as a drug target to fight human infections. Using peptides and peptidomimetics, we previously obtained proof of concept that disrupting protein–protein interactions at the dimer interface of Leishmania infantum TryR (LiTryR) offered an innovative and so far unexploited opportunity

  锥虫二硫化物还原酶 (TryR) 是锥虫寄生虫的一种必不可少的同型二聚酶，已被验证为对抗人类感染的药物靶点。使用肽和肽模拟物，我们之前获得了概念证明，即在婴儿利什曼原虫TryR (Li TryR )的二聚体界面上破坏蛋白质 - 蛋白质相互作用为开发新型抗利什曼原虫药物提供了一个创新且迄今为止尚未开发的机会。现在，我们表明将我们之前的肽原型TRL38 连接到选定的疏水部分提供了一系列新的小分子肽缀合物，它们可以作为Li TryR 活性和二聚化的良好抑制剂。
• Fierz; Sallmann, Helvetica Chimica Acta, 1922, vol. 5, p. 563
  作者：Fierz、Sallmann

  DOI：——

  日期：——
• Dutt, Journal of the Chemical Society, 1923, vol. 123, p. 226
  作者：Dutt

  DOI：——

  日期：——
• Schroeter; Roessler, Chemische Berichte, 1902, vol. 35, p. 4224
  作者：Schroeter、Roessler

  DOI：——

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

  DOI：——

  日期：——