2-[2-(3,4-Difluorophenyl)ethenyl]-8-hydroxyquinoline-7-carboxylic acid | 1227464-56-3

• 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: 2-[2-(3,4-Difluorophenyl)ethenyl]-8-hydroxyquinoline-7-carboxylic acid
• 英文别名: 2-[2-(3,4-difluorophenyl)ethenyl]-8-hydroxyquinoline-7-carboxylic acid
• CAS: 1227464-56-3
• 化学式: C₁₈H₁₁F₂NO₃
• 分子量: 327.287
• InChiKey: QMVWYWSCWDAVPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.42
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  8-羟基-2-甲基喹啉-7-羧酸 、 3,4-二氟苯甲醛 在 乙酸酐 、 吡啶 、 水 作用下， 生成 2-[2-(3,4-Difluorophenyl)ethenyl]-8-hydroxyquinoline-7-carboxylic acid
  参考文献：
  名称：

  In Vitro Activities of New 2-Substituted Quinolines against Leishmania donovani

  摘要：

  摘要 对一系列 9 种喹啉类和 18 种苯乙烯喹啉类药物的 体外 抗利什曼病活性和细胞毒性。7-aroylstyrylquinoline 支架似乎是最有前途的支架，其中最有趣的化合物是 No.35号化合物显示出50%的抑制浓度（IC 50 ）为 1.2 μM，选择性指数值为 121.5。与参考化合物米替福新和西他马喹相比，35 号化合物的活性分别提高了 10 倍和 8 倍，选择性指数分别提高了 607 倍和 60 倍。

  DOI：

  10.1128/aac.01299-10

文献信息

• Identification and structure–activity relationship of 8-hydroxy-quinoline-7-carboxylic acid derivatives as inhibitors of Pim-1 kinase
  作者：Faten Sliman、Mélina Blairvacq、Emilie Durieu、Laurent Meijer、Jordi Rodrigo、Didier Desmaële

  DOI：10.1016/j.bmcl.2010.03.061

  日期：2010.5

  Pim-1 kinase is a cytoplasmic serine/threonine kinase that controls programmed cell death by phosphorylating substrates that regulate both apotosis and cellular metabolism. A series of 2-styrylquinolines and quinoline-2-carboxamides has been identified as potent inhibitors of the Pim-1 kinase. The 8-hydroxyquinoline 7-carboxylic acid moiety appeared to be a crucial pharmacophore for activity. Molecular modeling indicated that interaction of this scaffold with Asp186 and Lys67 residues within the ATP-binding pocket might be responsible for the kinase inhibitory potency. (C) 2010 Elsevier Ltd. All rights reserved.
• <i>In Vitro</i> Activities of New 2-Substituted Quinolines against <i>Leishmania donovani</i>
  作者：Philippe M. Loiseau、Suman Gupta、Aditya Verma、Saumya Srivastava、S. K. Puri、Faten Sliman、Marie Normand-Bayle、Didier Desmaele

  DOI：10.1128/aac.01299-10

  日期：2011.4

  A series of 9 quinolines and 18 styrylquinolines was evaluated for the drugs' in vitro antileishmanial activities and cytotoxicities. The 7-aroylstyrylquinoline scaffold appeared to be the most promising one, with the most interesting compound, no. 35, exhibiting a 50% inhibitory concentration (IC ₅₀ ) of 1.2 μM and a selectivity index value of 121.5. Compound 35 was 10-fold and 8-fold more active than miltefosine and sitamaquine, the reference compounds, with selectivity indexes 607-fold and 60-fold higher, respectively.

  摘要 对一系列 9 种喹啉类和 18 种苯乙烯喹啉类药物的 体外 抗利什曼病活性和细胞毒性。7-aroylstyrylquinoline 支架似乎是最有前途的支架，其中最有趣的化合物是 No.35号化合物显示出50%的抑制浓度（IC 50 ）为 1.2 μM，选择性指数值为 121.5。与参考化合物米替福新和西他马喹相比，35 号化合物的活性分别提高了 10 倍和 8 倍，选择性指数分别提高了 607 倍和 60 倍。