3-amino-2-(4'-nitrobenzoyl)-5-(methylsulfonyl)thiophene-4-carbonitrile | 230310-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-2-(4'-nitrobenzoyl)-5-(methylsulfonyl)thiophene-4-carbonitrile
• 英文别名: 4-amino-5-(4-nitro-benzoyl)-2-methylsulfonyl-3-thiophene-carbonitril；4-Amino-2-methylsulfonyl-5-(4-nitrobenzoyl)thiophene-3-carbonitrile
• CAS: 230310-91-5
• 化学式: C₁₃H₉N₃O₅S₂
• 分子量: 351.364
• InChiKey: LPTHIFROWPQDFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  184
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-amino-2-(4'-nitrobenzoyl)-5-(methylsulfonyl)thiophene-4-carbonitrile 、 苯酚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 4-Amino-5-(4-nitrobenzoyl)-2-phenoxythiophene-3-carbonitrile
  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：

  4-amino-2-methylsulfanyl-5-(4-nitrobenzoyl)-3-thienyl cyanide 在 双氧水 、 溶剂黄146 作用下， 反应 336.0h， 以79%的产率得到3-amino-2-(4'-nitrobenzoyl)-5-(methylsulfonyl)thiophene-4-carbonitrile
  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

文献信息

• [EN] THIOPHENE DERIVATIVES AS MICROBICIDES AND HERBICIDES<br/>[FR] DERIVES DE THIOPHENE COMME MICROBICIDES ET HERBICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2004067527A1

  公开（公告）日：2004-08-12

  Novel thiophene derivatives of the formula (I) wherein R1, R2, R3 and n have the meanings given in the specification, several processes for the preparation of the new compounds and their use as microbicides and herbicides.

  本发明涉及一种新的噻吩衍生物，其化学式为（I），其中R1，R2，R3和n的含义如规范中所述，还涉及制备这些新化合物的几种方法以及它们作为微生物杀菌剂和除草剂的用途。
• 3-Amino-5-phenoxythiophenes:  Syntheses and Structure−Function Studies of a Novel Class of Inhibitors of Cellular <scp>l</scp>-Triiodothyronine Uptake
  作者：Detlef Briel、Dirk Pohlers、Mathias Uhlig、Silke Vieweg、Gerhard H. Scholz、Michael Thormann、Hans-Jörg Hofmann

  DOI：10.1021/jm980288r

  日期：1999.5.1

  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.

表征谱图