5-amino-1H-pyrazole-4-carboxylic acid (3-carbamoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-amide | 383379-51-9

• 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: 5-amino-1H-pyrazole-4-carboxylic acid (3-carbamoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-amide
• 英文别名: 5-amino-N-(3-carbamoyl-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-1H-pyrazole-4-carboxamide
• CAS: 383379-51-9
• 化学式: C₁₃H₁₅N₅O₂S
• 分子量: 305.36
• InChiKey: FXVCIYGXAVBCOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2-cyano-3-dimethylamino-acryloylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid amide 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以65%的产率得到5-amino-1H-pyrazole-4-carboxylic acid (3-carbamoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-amide
  参考文献：
  名称：

  基于4,5,6,7-四氢苯并噻吩基团的一些新型噻唑和吡唑衍生物的合成和抑菌活性

  摘要：

  通过2-（2-氰基-乙酰氨基）-4,5,6,7-四氢-苯并[b]噻吩-3-羧酰胺的反应分两步制备2-（5-氧噻唑啉酮）-氰基乙酰胺衍生物3（1）与异硫氰酸苯酯和氯乙酰氯，在吡啶中与对甲苯基重氮鎓氯化物重氮偶合，得到相应的肼基衍生物4。同样，3与对茴香醛缩合得到相应的芳基衍生物5。用硫酸二甲酯处理2，得到乙烯酮N，S-缩醛9，其得到5-氨基吡唑衍生物10用水合肼处理后。化合物10被用作关键中间体为吡唑并合成咪唑并[5,1-C] [1,2,4]三嗪13A，b，吡唑并[5,1-a]嘧啶14 - 17和pyrolo吡唑18个衍生物。最后，将1与DMF-DMA缩合，得到相应的丙烯酰胺衍生物19，当与水合肼一起加热时，得到相应的吡唑衍生物20。所有新合成的化合物均作为抗微生物剂进行了评估；他们中有些人表现出令人鼓舞的活动。

  DOI：

  10.1016/j.ejmech.2009.12.020

文献信息

• Heterobicyclic Compounds as Pharmaceutically Active Agents
  申请人：Koul Anil

  公开号：US20070275962A1

  公开（公告）日：2007-11-29

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteriainduced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.

  本文介绍了异杂双环化合物，例如4,5,6,7-四氢苯并[b]噻吩-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]硫杂吡喃-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]吡喃-3-羧酸酰胺，或苯并[b]噻吩-3-羧酸酰胺及其药学上可接受的盐。这些衍生物的用途包括预防和/或治疗各种疾病，如传染性疾病，包括分支杆菌感染和机会性疾病，朊病，免疫性疾病，自身免疫性疾病，双相和临床障碍，心血管疾病，细胞增殖性疾病，糖尿病，炎症，移植排斥，勃起功能障碍，神经退行性疾病和中风，以及含有至少一种异杂双环化合物和/或药学上可接受的盐的组合物。此外，还公开了合成异杂双环化合物的反应程序。
• THIOPHENE DERIVATIVES ACTIVE AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1294707A2

  公开（公告）日：2003-03-26
• [EN] THIOPHENE DERIVATIVES ACTIVE AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] DERIVES DE THIOPHENE ACTIFS EN TANT QU'INHIBITEURS DE KINASE, LEUR PROCEDE DE PREPARATION, ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：PHARMACIA & UPJOHN SPA

  公开号：WO2001098290A2

  公开（公告）日：2001-12-27

  Compounds which are 3-aminocarbonyl-2-carboxamido-thiophene derivatives or pharmaceutically acceptable salts thereof, together with pharmaceutical compositions comprising them are disclosed; these compounds or compositions are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, cell proliferative disorders, Alzheimer's disease, viral infections, auto-immune diseases and neurodegenerative disorders.
• Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety
  作者：M.A. Gouda、M.A. Berghot、Ghada E. Abd El-Ghani、A.M. Khalil

  DOI：10.1016/j.ejmech.2009.12.020

  日期：2010.4

  give 5-amino pyrazole derivative 10 upon treatment with hydrazine hydrate. Compound 10 was used as key intermediate for synthesis of pyrazolo[5,1-c][1,2,4]triazine 13a, b, pyrazolo[5,1-a]pyrimidine 14–17 and pyrolo pyrazole 18 derivatives. Finally, condensation of 1 with DMF-DMA afforded the corresponding acryloamide derivative 19, which afforded the corresponding pyrazole derivative 20 upon heating

  通过2-（2-氰基-乙酰氨基）-4,5,6,7-四氢-苯并[b]噻吩-3-羧酰胺的反应分两步制备2-（5-氧噻唑啉酮）-氰基乙酰胺衍生物3（1）与异硫氰酸苯酯和氯乙酰氯，在吡啶中与对甲苯基重氮鎓氯化物重氮偶合，得到相应的肼基衍生物4。同样，3与对茴香醛缩合得到相应的芳基衍生物5。用硫酸二甲酯处理2，得到乙烯酮N，S-缩醛9，其得到5-氨基吡唑衍生物10用水合肼处理后。化合物10被用作关键中间体为吡唑并合成咪唑并[5,1-C] [1,2,4]三嗪13A，b，吡唑并[5,1-a]嘧啶14 - 17和pyrolo吡唑18个衍生物。最后，将1与DMF-DMA缩合，得到相应的丙烯酰胺衍生物19，当与水合肼一起加热时，得到相应的吡唑衍生物20。所有新合成的化合物均作为抗微生物剂进行了评估；他们中有些人表现出令人鼓舞的活动。