N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide | 893388-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide
• 英文别名: N-(3-benzoyl-5-phenylthiophen-2-yl)acetamide
• CAS: 893388-14-2
• 化学式: C₁₉H₁₅NO₂S
• 分子量: 321.4
• InChiKey: WSUWFNPLWNHKNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 (2-amino-5-phenylthiophen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Effects of Conformational Restriction of 2-Amino-3-benzoylthiophenes on A₁ Adenosine Receptor Modulation

  摘要：

  2-Amino-3-benzoylthiophenes (2A3BTs) have been widely reported to act as allosteric enhancers (A Es) at the A(1) adenosine receptor (A(1)AR). Herein we describe the synthesis of a series of 1-aminoindeno[1,2-c]thiophen-8-ones and a series of (2-aminoindeno[2,1-b]thiophen-3-yl)(phenyl)methanones as conformationally rigid analogues of the 2A3BTs. These compounds were screened using a functional assay of A(1)AR-mediated phosphorylation of extracellular signal-regulated kinases 1 and 2 (ERK 1/2) in intact Chinese hamster ovary (CHO) cells to identify both potential agonistic effects as well as the ability to allosterically modulate the activity of the orthosteric agonist, N-6-(R-phenylisopropyl)adenosine (R-PIA). All of the 1-aminoindeno[1,2-c]thiophen-8-ones (14a-c and 17a-f) proved either to be inactive or behaved as antagonists in the functional assay. However, the (2-aminoindeno[2, 1-b]thiophen-3-yl)(phenyl)methanones with para-chloro substitution (compounds 25b, 25d, and 25f) did significantly augment the R-PIA response, indicating a positive allosteric effect.

  DOI：

  10.1021/jm1008538
• 作为产物：
  描述：

  N-(3-benzoyl-5-bromo-thiophen-2-yl)-acetamide 、 苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide
  参考文献：
  名称：

  WO2006/63732

  摘要：

  公开号：

文献信息

• Thieno-pyridine derivatives as allosteric enhancers of the GABAB receptors
  申请人：Malherbe Parichehr

  公开号：US20060135552A1

  公开（公告）日：2006-06-22

  The present invention relates to compounds of formula I wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in the specification. Compounds of the invention are active on the GABAB receptor and are useful for treating a variety of CNS disorders, including anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity-and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders and gastrointestinal disorders.

  本发明涉及式I化合物，其中R1、R2、R3、R4和R5如规范中所定义。本发明的化合物在GABAB受体上具有活性，并可用于治疗多种中枢神经系统疾病，包括焦虑、抑郁、癫痫、精神分裂症、认知障碍、痉挛和骨骼肌强直、脊髓损伤、多发性硬化症、肌萎缩性侧索硬化、脑瘫、神经病性疼痛和与可卡因和尼古丁有关的渴望、精神病、惊恐障碍、创伤后应激障碍和胃肠疾病。
• THIENO-PYRIDINE DERIVATIVES AS GABA-B ALLOSTERIC ENHANCERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1828199B1

  公开（公告）日：2009-05-06
• US7390903B2
  申请人：——

  公开号：US7390903B2

  公开（公告）日：2008-06-24
• [EN] THIENO-PYRIDINE DERIVATIVES AS GABA-B ALLOSTERIC ENHANCERS<br/>[FR] DERIVES DE LA THIENO-PYRIDINE RENFORÇATEURS ALLOSTERIQUES DU GABA-B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006063732A1

  公开（公告）日：2006-06-22

  [EN] The present invention relates to compounds of formula (I), Wherein R¹ to R⁵ are as defined in the specification which compounds are active on the GABA_B
  [FR] L'invention porte sur des composés de formule (I) dans laquelle: R¹ à R⁵ sont tels que définis dans les spécifications. Lesdits composés agissent sur le récepteur GABA_B
• WO2006/63732
  申请人：——

  公开号：——

  公开（公告）日：——