3-amino-4-cyano-5-(methylthio)thiophene-2-carboxamide | 39677-38-8

• 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: 3-amino-4-cyano-5-(methylthio)thiophene-2-carboxamide
• 英文别名: 3-amino-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid amide；3-Amino-4-cyano-5-methylsulfanylthiophene-2-carboxamide
• CAS: 39677-38-8
• 化学式: C₇H₇N₃OS₂
• 分子量: 213.284
• InChiKey: QJGQLUOMIQZHBM-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C(Solv: ethanol (64-17-5); 1,4-dioxane (123-91-1))
• 沸点：
  395.5±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-4-cyano-5-(methylthio)thiophene-2-carboxamide 在 双氧水 、 溶剂黄146 作用下， 反应 336.0h， 生成 3-Amino-4-cyano-5-methylsulfonylthiophene-2-carboxamide
  参考文献：
  名称：

  3-Amino-5-phenoxythiophenes:  Syntheses and Structure−Function Studies of a Novel Class of Inhibitors of Cellular l-Triiodothyronine Uptake

  摘要：

  A series of substituted 3-amino-5-phenoxythiophenes was synthesized starting from malodinitrile and carbon disulfide. The resulting dicyanoketenedithiolate reacts via Thorpe-Dieckmann cyclization with halogen methanes bearing electron-withdrawing groups to give thiophene-2-thiolates, which can be transformed into 3-amino-5-(methylsulfonyl)thiophene-4-carbonitriles. Replacement of the methylsulfonyl groups by substituted phenolates provides the substituted 3-amino-5-phenoxythiophenes. Some of the derivatives show a considerable inhibitory potency for the L-T-3 uptake in inhibition studies on human HepG2 hepatoma cells with maximum values of about 60% at a dose of 10(-5) M for the most potent 2-benzoyl derivatives. The structure of the phenoxythiophenes fits well into a general concept derived for other classes of L-T-3 uptake inhibitors, which postulates an angular and perpendicular orientation of the ring systems in these compounds as a prerequisite for an inhibitory potency. Docking studies for the phenoxythiophenes with transthyretin as a receptor model show their preferred attack at the L-T-4/L-T-3 binding channel.

  DOI：

  10.1021/jm980288r
• 作为产物：
  描述：

  Thieno(2,3-c)isothiazole-5-carboxamide, 4-amino-3-(methylthio)- 以 乙醇 为溶剂， 反应 120.0h， 生成 3-amino-4-cyano-5-(methylthio)thiophene-2-carboxamide
  参考文献：
  名称：

  Corsaro, Antonino; Guerrera, Francesco; Sarva, Maria C., Heterocycles, 1988, vol. 27, # 10, p. 2539 - 2544

  摘要：

  DOI：

文献信息

• Compositions useful as inhibitors of GSK-3
  申请人：——

  公开号：US20030096813A1

  公开（公告）日：2003-05-22

  The present invention provides compounds of formula I: 1 or a pharmaceutically acceptable derivative thereof, wherein X is oxygen or sulfur; Y is —S—, —O—, or —NR 1 —; and R 2 , R 3 , and R 4 are as described in the specification. These compounds are inhibitors of protein kinase, particularly inhibitors of GSK-3 mammalian protein kinase. The invention also provides pharmaceutical compositions comprising the inhibitors of the invention and methods of utilizing those compositions in the treatment and prevention of various disorders, such as diabetes and Alzheimer's disease.

  本发明提供了公式I:1的化合物或其药学上可接受的衍生物，其中X为氧或硫；Y为—S—、—O—或—NR1—；而R2、R3和R4如说明书中所述。这些化合物是蛋白激酶的抑制剂，特别是GSK-3哺乳动物蛋白激酶的抑制剂。该发明还提供了包含该发明的抑制剂的药物组合物，并提供了利用这些组合物在治疗和预防各种疾病，如糖尿病和阿尔茨海默病中的方法。
• Gaber, Hatem M.; Hafiz, Ibrahim S. Abdel; Elsawy, Karim M., Acta Chimica Slovenica, 2010, vol. 57, # 1, p. 230 - 243
  作者：Gaber, Hatem M.、Hafiz, Ibrahim S. Abdel、Elsawy, Karim M.、Sherif, Sherif M.

  DOI：——

  日期：——
• CORSARO, ANTONINO;GUERRERA, FRANCESCO;SARVA, MARIA C.;SIRACUSA, MARIA A., HETEROCYCLES, 27,(1988) N1, C. 2539-2544
  作者：CORSARO, ANTONINO、GUERRERA, FRANCESCO、SARVA, MARIA C.、SIRACUSA, MARIA A.

  DOI：——

  日期：——
• 9-DEAZAGUANINE DERIVATIVES AS INHIBITORS OF GSK-3
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP1383771A1

  公开（公告）日：2004-01-28
• [EN] 9-DEAZAGUANINE DERIVATIVES AS INHIBITORS OF GSK-3<br/>[FR] DERIVES DE 9-DEAZAGUANINE UTILISES COMME INHIBITEURS DE LA GSK-3
  申请人：VERTEX PHARMA

  公开号：WO2002085909A1

  公开（公告）日：2002-10-31

  The present invention provides compounds of formula I:or a pharmaceutically acceptable derivative thereof, wherein X is oxygen or sulfur; Y is -S-, -O- or -NR1-; and R2, R3, and R4 are as described in the specification. These compounds are inhibitors of protein kinase, particularly inhibitors of GSK-3 mammalian protein kinase. The invention also provides pharmaceutical compositions comprising the inhibitors of the invention and methods of utilizing those compositions in the treatement and prevention of various disorders, such as diabetes and Alzheimer's disease.