1-[1-diethylamino-1-phenylmeth-(E)-ylidene]-3-(4-methylbenzoyl)thiourea | 952612-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[1-diethylamino-1-phenylmeth-(E)-ylidene]-3-(4-methylbenzoyl)thiourea
• 英文别名: N-[(E)-[diethylamino(phenyl)methylidene]carbamothioyl]-4-methylbenzamide
• CAS: 952612-56-5
• 化学式: C₂₀H₂₃N₃OS
• 分子量: 353.488
• InChiKey: XYKVHBFPQGRDBW-DYTRJAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[1-diethylamino-1-phenylmeth-(E)-ylidene]-3-(4-methylbenzoyl)thiourea 、 6-(氯甲基)-N,N-二甲基-1,3,5-三嗪-2,4-二胺 以 甲醇 为溶剂， 反应 24.0h， 以39%的产率得到N-(5-(4-amino-6-(dimethylamino)-1,3,5-triazin-2-yl)-4-phenylthiazol-2-yl)-4-methylbenzamide
  参考文献：
  名称：

  New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

  摘要：

  A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A(2A) adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.020
• 作为产物：
  描述：

  苯甲腈 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 1-[1-diethylamino-1-phenylmeth-(E)-ylidene]-3-(4-methylbenzoyl)thiourea
  参考文献：
  名称：

  New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

  摘要：

  A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A(2A) adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.020

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.