5-[4-(methylsulfanyl)phenyl]-1H-pyrazol-3-amine | 208519-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[4-(methylsulfanyl)phenyl]-1H-pyrazol-3-amine
• 英文别名: 3-amino-5-(4-methylthiophenyl)pyrazole；5-(4-methylsulfanylphenyl)-1H-pyrazol-3-amine
• CAS: 208519-14-6
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: MOPGQVQDCKMELZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[4-(methylsulfanyl)phenyl]-1H-pyrazol-3-amine 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 93.5h， 生成 N-[1-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-5-(4-methylsulfonylphenyl)pyrazol-3-yl]acetamide;hydrochloride
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 盐酸 、 pyridinium hydrobromide perbromide 、 氢溴酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 5-[4-(methylsulfanyl)phenyl]-1H-pyrazol-3-amine
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048

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