[5-benzyl-3-(3-fluorophenyl)-4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester | 851853-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: [5-benzyl-3-(3-fluorophenyl)-4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester
• 英文别名: Ethyl 2-[[5-benzyl-3-(3-fluorophenyl)-4-oxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl]sulfanyl]acetate
• CAS: 851853-14-0
• 化学式: C₂₇H₂₅FN₂O₃S₂
• 分子量: 508.638
• InChiKey: GBNLCCYEMSAFAP-UHFFFAOYSA-N

物化性质

• 沸点：
  661.9±65.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [5-benzyl-3-(3-fluorophenyl)-4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester 在 肼 作用下， 以 乙醇 为溶剂， 生成 [5-benzyl-3-(3-fluorophenyl)-4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid hydrazide
  参考文献：
  名称：

  Structure–activity relationship study of novel tissue transglutaminase inhibitors

  摘要：

  Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative alpha-N-Boc-Lys-CH2-CH2-dansyl into the protein substrate N,N-dimethylated-casein. A SAR study revealed that the acylhydrazide thioether side-chain and the thiophene ring were critical to inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.005
• 作为产物：
  描述：

  2-苄基环己酮 在 吗啉 、 吡啶 、 sodium methylate 、 potassium carbonate 、 sulfur 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [5-benzyl-3-(3-fluorophenyl)-4-oxo-3,4,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester
  参考文献：
  名称：

  Structure–activity relationship study of novel tissue transglutaminase inhibitors

  摘要：

  Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative alpha-N-Boc-Lys-CH2-CH2-dansyl into the protein substrate N,N-dimethylated-casein. A SAR study revealed that the acylhydrazide thioether side-chain and the thiophene ring were critical to inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.005

文献信息

• Tissue transglutaminase inhibitors
  申请人：Stein L. Ross

  公开号：US20060183759A1

  公开（公告）日：2006-08-17

  The present invention provides novel compounds and methods useful for treating transglutaminase associated disorders such as celiac spru, Alzheimer's disease and Huntington's disease. Certain compounds of the invention are tissue transglutaminase inhibitors that comprise thiophene moieties. Methods of the invention include treatment of transglutaminase associated disorders with inhibitors of transglutaminase.

  本发明提供了一种治疗转酰胺酶相关疾病的新化合物和方法，例如腹泻性脆皮病、阿尔茨海默病和亨廷顿病。本发明的某些化合物是组织转酰胺酶抑制剂，包括噻吩基团。本发明的方法包括使用转酰胺酶抑制剂治疗转酰胺酶相关疾病。
• Structure–activity relationship study of novel tissue transglutaminase inhibitors
  作者：Eric Duval、April Case、Ross L. Stein、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2005.02.005

  日期：2005.4

  Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative alpha-N-Boc-Lys-CH2-CH2-dansyl into the protein substrate N,N-dimethylated-casein. A SAR study revealed that the acylhydrazide thioether side-chain and the thiophene ring were critical to inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.