3-(4-Methylthiophen-2-yl)-1H-pyrazol-5-amine | 1440809-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 3-(4-Methylthiophen-2-yl)-1H-pyrazol-5-amine
• 英文别名: 5-(4-methylthiophen-2-yl)-1H-pyrazol-3-amine
• CAS: 1440809-87-9
• 化学式: C₈H₉N₃S
• 分子量: 179.246
• InChiKey: BYZQSCGRKNMTBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Methylthiophen-2-yl)-1H-pyrazol-5-amine 在 水 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.17h， 生成 N-(1-adamantyl)-2-(4-methylthiophen-2-yl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

  摘要：

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

  DOI：

  10.1021/jm400182t

文献信息

• PYRAZOLE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0945438A1

  公开（公告）日：1999-09-29

  The present invention relates to a compound represented by the general formula [I]: wherein A and B rings are ortho-condensed to each other, A ring represents an aromatic carbocyclic or heterocyclic ring and B ring represents an aliphatic four- to seven-membered carbocyclic or nitrogen-containing heterocyclic ring, said nitrogen atom being possible to present at only the position where the A ring is condensed; Ar represents an aromatic carbocyclic or heterocyclic ring group which may have a substituent selected from the group consisting of a halogen atom and lower alkyl, lower alkenyl, lower haloalkyl, lower alkoxy, lower alkylthio, lower alkylamino, lower dialkylamino and aromatic carbocyclic ring groups; and R represents a substituent selected from the group consisting of a halogen atom and nitro, lower alkyl, lower alkoxy, aromatic carbocyclic ring groups and a carbonyl group having an aromatic carbocyclic ring group, or a hydrogen atom, provided that when the group represented by is the group represented by Ar is not a phenyl group nor a 4-chlorophenyl group, or its salt, a method for its preparation as well as an agent for the treatment of bulimia, obesity or diabetes comprising it as an active ingredient.

  本发明涉及通式[I]代表的化合物： 其中 A 环和 B 环彼此正交缩合，A 环代表芳香族碳环或杂环，B 环代表脂肪族四至七元碳环或含氮杂环，所述氮原子可能仅存在于 A 环缩合的位置；Ar 代表芳香碳环或杂环基团，其取代基可选自由卤素原子、低级烷基、低级烯基、低级卤代烷基、低级烷氧基、低级烷硫基、低级烷氨基、低级二烷基氨基和芳香碳环基团组成的组；和 R 代表选自卤素原子和硝基、低级烷基、低级烷氧基、芳香族碳环基团和具有芳香族碳环基团的羰基或氢原子的取代基，条件是当由 代表的基团 Ar 不是苯基，也不是 4-氯苯基、 或其盐，其制备方法以及治疗暴食症、肥胖症或糖尿病的药物，其活性成分均包含该物质。
• NOVEL UREA DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0955293A1

  公开（公告）日：1999-11-10

  The present invention relates to a compound represented by the general formula [I]: wherein A represents a nitrogen atom or a group represented by C-R5; Ar1 represents an aryl group which may have a substituent selected from the group consisting of a halogen atom and lower alkyl and lower haloalkyl groups; Ar2 represents an aryl or heteroaryl group which may have a substituent selected from the group consisting of a halogen atom and lower alkyl, lower alkenyl, lower haloalkyl, lower alkoxy, lower alkylthio, lower alkylamino, lower dialkylamino and aryl groups; R1 represents a hydrogen atom, a lower alkyl group or a bond formed by linking to R5; R2 represents a hydrogen atom or a lower alkyl group; R3 and R4 may be the same or different and each represents a hydrogen atom or a lower alkyl group, or R3 and R4 are linked to each other to form an alkylene group containing 2 to 4 carbon atoms which may have a lower alkyl group; and R5 represents a hydrogen atom or a hydroxyl, lower alkyl or lower alkoxy group or a bond formed by linking to R1, or its salt, a process for its preparation and an agent for the treatment of bulimia, obesity or diabetes comprising it as an active ingredient.

  本发明涉及通式[I]所代表的化合物： 其中A代表氮原子或由C-R5代表的基团；Ar1代表芳基，其取代基可选自卤素原子和低级烷基及低级卤代烷基组成的组；Ar2代表芳基或杂芳基，其取代基可选自卤素原子和低级烷基、低级烯基、低级卤代烷基、低级烷氧基、低级烷硫基、低级烷基氨基、低级二烷基氨基和芳基组成的组；R1 代表氢原子、低级烷基或与 R5 连接形成的键；R2 代表氢原子或低级烷基；R3 和 R4 可以相同或不同，且各自代表氢原子或低级烷基，或 R3 和 R4 相互连接形成含 2 至 4 个碳原子的亚烷基，该亚烷基可能具有低级烷基；以及 R5 代表氢原子或羟基、低级烷基或低级烷氧基或与 R1 连接形成的键、 或其盐类，其制备方法和治疗贪食症、肥胖症或糖尿病的制剂，其活性成分包括它。
• UREA DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0955293B1

  公开（公告）日：2003-03-19
• US6043246A
  申请人：——

  公开号：US6043246A

  公开（公告）日：2000-03-28
• US6057335A
  申请人：——

  公开号：US6057335A

  公开（公告）日：2000-05-02