ethyl 2-amino-4-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate | 60598-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 2-amino-4-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
• 英文别名: 2-amino-4-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid ethyl ester；Ethyl 2-amino-4-phenyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS: 60598-70-1
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: WHMSKQZARDTHCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 在 吡啶 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [3-(3-fluorophenyl)-4-oxo-5-phenyl-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
• 作为产物：
  描述：

  ethyl 2-cyano-2-(2-phenylcyclohexylidene)acetate 在 吗啉 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以79%的产率得到ethyl 2-amino-4-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  [EN] FUSED THIOPHENE DERIVATIVES AND THEIR USES
  [FR] DÉRIVÉS DE THIOPHÈNE CONDENSÉS ET LEURS UTILISATIONS

  摘要：

  本发明涉及一类新的融合噻吩衍生物，以及它们在治疗感染、癌症、代谢性疾病、心血管疾病、铁储存障碍和炎症性疾病方面的用途。

  公开号：

  WO2019154949A1

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。
• FUSED THIOPHENE DERIVATIVES AND THEIR USES
  申请人：ENYO Pharma

  公开号：EP3749658A1

  公开（公告）日：2020-12-16
• [EN] SUBSTITUED 3,4-DIHYDROTHIENO [2,3-D] PYRMIDINES AS TISSUE TRANSGLUTAMINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TRANSGLUTAMINASE TISSULAIRE
  申请人：BRIGHAM & WOMENS HOSPITAL

  公开号：WO2006060702A1

  公开（公告）日：2006-06-08

  [EN] 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.
  [FR] L'invention concerne de nouveaux composés et méthodes permettant de traiter des troubles associés à la transglutaminase, tels que la maladie coeliaque, la maladie d'Alzheimer et la maladie de Huntington. Certains composés selon l'invention possèdent des inhibiteurs de la transglutaminase tissulaire qui comprennent des fractions thiophène. Des méthodes selon l'invention comprennent le traitement des troubles associés à la transglutaminase à l'aide des inhibiteurs de la transglutaminase.
• 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.
• [EN] FUSED THIOPHENE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS DE THIOPHÈNE CONDENSÉS ET LEURS UTILISATIONS
  申请人：ENYO PHARMA

  公开号：WO2019154949A1

  公开（公告）日：2019-08-15

  The present invention relates to a new class of fused thiophene derivatives and their uses for treating diseases such as infection, cancer, metabolic diseases, cardiovascular diseases, iron storage disorders and inflammatory disorders.

  本发明涉及一类新的融合噻吩衍生物，以及它们在治疗感染、癌症、代谢性疾病、心血管疾病、铁储存障碍和炎症性疾病方面的用途。