5-[5-(2-Chlorophenyl)furan-2-ylmethylene]thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-[5-(2-Chlorophenyl)furan-2-ylmethylene]thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₄H₈ClNO₃S
• 分子量: 305.741
• InChiKey: UKOAKDJZVZQHAH-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 5-(2-氯苯基)-2-呋喃甲醛 生成 5-[5-(2-Chlorophenyl)furan-2-ylmethylene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Aryl-link-aryl substituted thiazolidine-dione and oxazolidine-dione as sodium channel blockers

  摘要：

  Aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物是钠通道阻滞剂; 包括有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物以及药学上可接受的载体的制药组合物，以及通过给予有效量的aryl-link-aryl噻唑烷二酮和aryl-link-aryl噁唑烷二酮化合物治疗急性疼痛，慢性疼痛，内脏疼痛，炎症性疼痛或神经痛，以及初始性肠道综合症，克罗恩病，癫痫，部分和全身性强直性发作，多发性硬化症，双相抑郁症和快速心律失常的方法。

  公开号：

  US07348348B2

文献信息

• Furan-2-ylmethylene Thiazolidinediones as Novel, Potent, and Selective Inhibitors of Phosphoinositide 3-Kinase γ
  作者：Vincent Pomel、Jasna Klicic、David Covini、Dennis D. Church、Jeffrey P. Shaw、Karen Roulin、Fabienne Burgat-Charvillon、Delphine Valognes、Montserrat Camps、Christian Chabert、Corinne Gillieron、Bernard Françon、Dominique Perrin、Didier Leroy、Denise Gretener、Anthony Nichols、Pierre Alain Vitte、Susanna Carboni、Christian Rommel、Matthias K. Schwarz、Thomas Rückle

  DOI：10.1021/jm0601598

  日期：2006.6.1

  Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3K gamma, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3K gamma inhibitors. Structure-based design and X-ray crystallography of complexes formed by inhibitors bound to PI3K gamma identified key pharmacophore features for potency and selectivity. An acidic NH group on the thiazolidinedione moiety and a hydroxy group on the furan-2-yl-phenyl part of the molecule play crucial roles in binding to PI3K and contribute to class IB PI3K selectivity. Compound 26 (AS-252424), a potent and selective small-molecule PI3K gamma inhibitor emerging from these efforts, was further profiled in three different cellular PI3K assays and shown to be selective for class IB PI3K-mediated cellular effects. Oral administration of 26 in a mouse model of acute peritonitis led to a significant reduction of leukocyte recruitment.
• EP1501509A4
  申请人：——

  公开号：EP1501509A4

  公开（公告）日：2009-07-15
• ARYL-LINK-ARYL SUBSTITUTED THIAZOLIDINE-DIONE AND OXAZOLIDINE-DIONE AS SODIUM CHANNEL BLOCKERS
  申请人：Merck & Co., Inc.

  公开号：EP1501509A2

  公开（公告）日：2005-02-02
• US7348348B2
  申请人：——

  公开号：US7348348B2

  公开（公告）日：2008-03-25
• [EN] ARYL-LINK-ARYL SUBSTITUTED THIAZOLIDINE-DIONE AND OXAZOLIDINE-DIONE AS SODIUM CHANNEL BLOCKERS<br/>[FR] THIAZOLIDINE-DIONE ET OXAZOLIDINE-DIONE A SUBSTITUTION ARYLE-LIAISON-ARYLE UTILES EN TANT QUE BLOQUEURS DES CANAUX SODIQUES
  申请人：MERCK & CO INC

  公开号：WO2004024061A2

  公开（公告）日：2004-03-25

  Aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are sodium channel blockers; pharmaceutical compositions that include an effective amount of the aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds and a pharmaceutically acceptable carrier; and a method of treatment of acute pain, chronic pain, visceral pain, inflammatory pain, or neuropathic pain, as well as irritable bowel syndrome, Crohns disease, epilepsy, partial and generalized tonic seizures, multiple sclerosis, bipolar depression, and tachy-arrhythmias by the administration of an effective amount of aryl-link-aryl thiazolidine-dione and aryl-link-aryl oxazolidine-dione compounds are described.