3-(2-chloro-phenyl)-2-[2-(4-chloro-phenylamino)-4-methyl-thiazol-5-yl]-3H-quinazolin-4-one | 952613-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(2-chloro-phenyl)-2-[2-(4-chloro-phenylamino)-4-methyl-thiazol-5-yl]-3H-quinazolin-4-one
• 英文别名: 2-[2-(4-chlorophenylamino)-4-methyl-thiazol-5-yl]-3-(2-chloro-phenyl)-3H-quinazolin-4-one；2-[2-(4-Chloroanilino)-4-methyl-1,3-thiazol-5-yl]-3-(2-chlorophenyl)quinazolin-4-one
• CAS: 952613-30-8
• 化学式: C₂₄H₁₆Cl₂N₄OS
• 分子量: 479.389
• InChiKey: VLFNQZMEZRAGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-Chlorophenyl)-3-[1-(diethylamino)ethylidene]thiourea 、 2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one 以 乙腈 为溶剂， 以41%的产率得到3-(2-chloro-phenyl)-2-[2-(4-chloro-phenylamino)-4-methyl-thiazol-5-yl]-3H-quinazolin-4-one
  参考文献：
  名称：

  Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents

  摘要：

  A series of 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives were designed and synthesized. Synthesized molecules were further evaluated for their inhibitory activity towards transcription factors NF-kappa B and AP-1 mediated transcriptional activation in a cell line based in vitro as well as for their anti-inflammatory activity in in vivo model of acute inflammation. This series provides us with selective and dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation which also exhibit significant efficacy in in vivo model of inflammation. Two of the compounds 9m and 9o turned out to be the most promising dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation with an IC50 of 3.3 mu M for both. 9n (IC50 = 5.5 mu M) and 9p (IC50 = 5.5 mu M) emerged as selective inhibitors of NF-kappa B mediated transcriptional activation and 9c (IC50 = 5.5 mu M) and 9d (IC50 = 5.5 mu M) were found to be more selective inhibitor of AP-1 mediated transcriptional activity. Though the relationship between the activities shown by these compounds in in vivo and in vitro model is still to be established, these results suggest the suitability of the designed molecular framework as a potential anti-inflammatory molecular framework which also exhibits the inhibitory activity towards NF-kappa B and AP-1 mediated transcriptional activation. This will be worth studying further to explore its complete potential particularly in chronic inflammatory conditions. The structure activity relationship (SAR) of this series has been discussed herein. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.031

文献信息

• THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS
  申请人：Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College

  公开号：EP2007393A2

  公开（公告）日：2008-12-31
• Thiazole and Thiophene Analogues, and Their Use in Treating Autoimmune Diseases and Cancers
  申请人：Giordano Anthony

  公开号：US20090306073A1

  公开（公告）日：2009-12-10

  Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
• US8217037B2
  申请人：——

  公开号：US8217037B2

  公开（公告）日：2012-07-10
• US8829014B2
  申请人：——

  公开号：US8829014B2

  公开（公告）日：2014-09-09
• [EN] THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS<br/>[FR] THIAZOLE ET THIOPHENE ANALOGUES ET LEUR UTILISATION POUR TRAITER DES MALADIES AUTO-IMMUNES ET DES CANCERS
  申请人：UNIV LOUISIANA STATE

  公开号：WO2007118149A2

  公开（公告）日：2007-10-18

  [EN] Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
  [FR] La présente invention concerne des composés de thiazole et de thiophène utilisables pour traiter des inflammations, des états immuno-inflammatoires, des maladies auto-immunes et des cancers. L'invention concerne également des procédés de synthèse de ces composés.