methyl 3-amino-4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate | 129332-44-1

• 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: methyl 3-amino-4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate
• 英文别名: Methyl 3-amino-4-cyano-5-methylsulfonylthiophene-2-carboxylate
• CAS: 129332-44-1
• 化学式: C₈H₈N₂O₄S₂
• 分子量: 260.295
• InChiKey: DOAVLHDNNBIYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到Methyl 3-amino-4-cyano-5-hydrazinylthiophene-2-carboxylate
  参考文献：
  名称：

  Briel, Pharmazie, 1995, vol. 50, # 10, p. 675 - 678

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基-4-氰基-5-巯基噻吩-2-羧酸甲酯 在 双氧水 、 sodium methylate 作用下， 以 溶剂黄146 为溶剂， 反应 170.0h， 生成 methyl 3-amino-4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate
  参考文献：
  名称：

  Briel, Pharmazie, 1995, vol. 50, # 10, p. 675 - 678

  摘要：

  DOI：

文献信息

• [EN] THIOPHENES AND THEIR USE AS PHOSPHATIDYLINOSITOL 3-KINASE (PI3K) INHIBITORS<br/>[FR] THIOPHÈNES ET LEURS UTILISATIONS
  申请人：MILLENNIUM PHARM INC

  公开号：WO2009094224A1

  公开（公告）日：2009-07-30

  This invention provides thiophene compounds of formula (I) : wherein R1, R2, R3, R4, n, p, and m are as described in the specification. The compounds are inhibitors of PI3K and are thus useful for treating proliferative, inflammatory, or cardiovascular disorders.

  这项发明提供了式（I）的噻吩化合物：其中R1、R2、R3、R4、n、p和m如规范中所述。这些化合物是PI3K的抑制剂，因此可用于治疗增殖性、炎症性或心血管疾病。
• A-ring modifications on the triazafluorenone core structure and their mGluR1 antagonist properties
  作者：T.K. Sasikumar、Li Qiang、Duane A. Burnett、William J. Greenlee、Cheng Li、Mariagrazia Grilli、Rosalia Bertorelli、Gianluca Lozza、Angelo Reggiani

  DOI：10.1016/j.bmcl.2010.03.004

  日期：2010.4

  A-ring modifications on the triazafluorenone core structure were investigated. Five membered heterocycles such as pyrazoles and isothiazoles are not tolerated. It has been found that the pyrimidine nucleus was very well tolerated on the left hand side. Amino pyrimidine compounds 24 and 27 showed acceptable PK profile with significant brain penetration. Compound 9 served as a versatile intermediate

  研究了三氮杂芴酮核心结构上的A环修饰。不允许使用五元杂环，例如吡唑和异噻唑。已经发现，嘧啶核在左手侧具有很好的耐受性。氨基嘧啶化合物24和27表现出可接受的PK分布，并具有明显的脑部渗透能力。化合物9用作许多化学转化的通用中间体。
• Thiophenes and uses thereof
  申请人：Renou Christelle C.

  公开号：US20090325925A1

  公开（公告）日：2009-12-31

  This invention provides thiophene compounds of formula I: wherein R 1 , R 2 , R 3 , R 4 , n, p, and m are as described in the specification. The compounds are inhibitors of PI3K and are thus useful for treating proliferative, inflammatory, or cardiovascular disorders.

  本发明提供了公式I中的噻吩化合物：其中R1、R2、R3、R4、n、p和m如说明书所述。这些化合物是PI3K的抑制剂，因此可用于治疗增殖性、炎症性或心血管疾病。
• Briel, Pharmazie, 1998, vol. 53, # 4, p. 227 - 231
  作者：Briel

  DOI：——

  日期：——
• 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.