6-(3-hydroxyphenyl)indolin-2-one | 1246957-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(3-hydroxyphenyl)indolin-2-one
• 英文别名: 6-(3-Hydroxyphenyl)-1,3-dihydroindol-2-one
• CAS: 1246957-54-9
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: PMOXDHLGLYJPAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-formyl-2-methylselenophene-3-carboxylic acid 、 6-(3-hydroxyphenyl)indolin-2-one 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (Z)-5-((6-(3-hydroxyphenyl)-2-oxoindolin-3-ylidene)methyl)-2-methylselenophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of selenophene derivatives as novel CHK1 inhibitors

  摘要：

  A series of selenophene derivatives 3 were synthesized as potential CHK1 inhibitors. The effects of substitution on the 4'- or 5'-position of selenophene moiety and shifting the hydroxyl group position on C6-phenolic ring of oxindole were explored. This study led to the discovery of the most potent CHK1 inhibitors 29-33 and 39-43, which had IC(50) values in the subnanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.034
• 作为产物：
  描述：

  在 盐酸 、 tin 作用下， 生成 6-(3-hydroxyphenyl)indolin-2-one
  参考文献：
  名称：

  Synthesis of selenophene derivatives as novel CHK1 inhibitors

  摘要：

  A series of selenophene derivatives 3 were synthesized as potential CHK1 inhibitors. The effects of substitution on the 4'- or 5'-position of selenophene moiety and shifting the hydroxyl group position on C6-phenolic ring of oxindole were explored. This study led to the discovery of the most potent CHK1 inhibitors 29-33 and 39-43, which had IC(50) values in the subnanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.034

文献信息

• [EN] TRUXILLIC ACID MONOESTER-DERIVATIVES AS SELECTIVE FABP5 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] DÉRIVÉS MONOESTERS DE L'ACIDE TRUXILLIQUE UTILISÉS COMME INHIBITEURS SÉLECTIFS DE FABP5 ET COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2022076820A1

  公开（公告）日：2022-04-14

  The present invention provides a compound, and method of selectively inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, said compound having the structure:

  本发明提供了一种化合物和一种选择性抑制脂肪酸结合蛋白（FABP）活性的方法，该方法包括将该化合物与FABP接触，该化合物具有以下结构：
• SAR study on Novel truxillic acid monoester-Based inhibitors of fatty acid binding proteins as Next-Generation antinociceptive agents
  作者：Hehe Wang、Adam Taouil、Monaf Awwa、Timothy Clement、Chuanzhou Zhu、Jinwoo Kim、Dominick Rendina、Kalani Jayanetti、Atri Maharaj、Liqun Wang、Diane Bogdan、Antonella Pepe、Martin Kaczocha、Iwao Ojima

  DOI：10.1016/j.bioorg.2022.106184

  日期：2022.12

  Fatty acid binding protein 5 (FABP5) is a highly promising target for the development of analgesics as its inhibition is devoid of CB1R-dependent side-effects. The design and discovery of highly potent and FABP5-selective truxillic acid (TA) monoesters (TAMEs) is the primary aim of the present study. On the basis of molecular docking analysis, ca. 2,000 TAMEs were designed and screened in silico, to

  脂肪酸结合蛋白 5 (FABP5) 是镇痛药开发中非常有前景的靶标，因为它的抑制作用没有 CB 1 R 依赖性副作用。设计和发现高效且 FABP5 选择性的 truxillic 酸 (TA) 单酯 (TAME) 是本研究的主要目的。根据分子对接分析，大约。通过计算机设计和筛选了 2,000 种 TAME，最终汇集了 55 种新的 TAME，合成了这些 TAME，并分析了它们与 FABP5、3 和 7 的亲和力 (Ki)。SAR 研究表明，将氢键受体引入到远端1,1'-联苯-3-基和 1,1'-联苯-2-基酯部分的末端提高了 α-TAME 与 FABP5 的亲和力。化合物γ -3是第一个γ-TAME，表现出对FABP5 的高亲和力并与α-TAME 竞争。我们根据 FABP5/3 选择性指数确定了最好的 20 个 TAME。明显的领先者是α-16 ，带有 2-茚满酯部分。与此形成鲜明对比的是，没有