7-(furan-3-yl)indoline-2,3-dione | 851519-98-7

• 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: 7-(furan-3-yl)indoline-2,3-dione
• 英文别名: 7-furan-3-yl-1H-indole-2,3-dione；7-(Furan-3-yl)-1H-indole-2,3-dione
• CAS: 851519-98-7
• 化学式: C₁₂H₇NO₃
• 分子量: 213.192
• InChiKey: QXOILONAAYLDMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(furan-3-yl)indoline-2,3-dione 、 1-(乙酰氧基)-3-(4-氯苯基)-2-丙酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以15%的产率得到2-(4-chlorobenzyl)-8-(fur-3-yl)-3-hydroxyquinoline-4-carboxylic acid
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p
• 作为产物：
  描述：

  (2Z)-2-hydroxyimino-N-(2-iodophenyl)acetamide 在 四(三苯基膦)钯 硫酸 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 生成 7-(furan-3-yl)indoline-2,3-dione
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p

文献信息

• Methods and compositions for selectin inhibition
  申请人：Kaila Neelu

  公开号：US20050101568A1

  公开（公告）日：2005-05-12

  The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula I: wherein the constituent variables are defined herein.

  本发明涉及抗炎物质领域，更特别地涉及作为哺乳动物粘附蛋白拮抗剂的新化合物。在某些实施例中，提供了治疗选择素介导疾病的方法，包括给予式I的化合物： 其中组分变量在此处定义。
• Methods and Compositions for Selectin Inhibition
  申请人：Kaila Neelu

  公开号：US20090076077A1

  公开（公告）日：2009-03-19

  The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selecting. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula I: wherein the constituent variables are defined herein.

  本发明涉及抗炎物质领域，更具体地涉及新型化合物，其作为哺乳动物粘附蛋白（称为选择素）拮抗剂。在某些实施例中，提供了用于治疗选择素介导的疾病的方法，其中包括给予式I化合物的给药，其中组成变量在此定义。
• METHODS AND COMPOSITIONS FOR SELECTIN INHIBITION
  申请人：Wyeth

  公开号：EP1682511A2

  公开（公告）日：2006-07-26
• US7465799B2
  申请人：——

  公开号：US7465799B2

  公开（公告）日：2008-12-16
• [EN] METHODS AND COMPOSITIONS FOR SELECTIN INHIBITION<br/>[FR] METHODES ET COMPOSITIONS POUR INHIBER LA SELECTINE
  申请人：WYETH CORP

  公开号：WO2005047257A2

  公开（公告）日：2005-05-26

  The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula: (I) wherein the constituent variables are defined herein.