3-(3,4-二氯苯基)-1H-吡唑-5-胺 | 208519-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(3,4-二氯苯基)-1H-吡唑-5-胺
• 英文名称: 5-(3,4-dichloro-phenyl)-1H-pyrazol-3-ylamine
• 英文别名: 3-amino-5-(3,4-dichlorophenyl)pyrazole；5-(3,4-dichlorophenyl)-1H-pyrazol-3-amine
• CAS: 208519-10-2
• 化学式: C₉H₇Cl₂N₃
• mdl: MFCD02572047
• 分子量: 228.081
• InChiKey: YKEDJVVQHWJYBR-UHFFFAOYSA-N

物化性质

• 沸点：
  491.7±45.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,4-二氯苯基)-1H-吡唑-5-胺 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 7-(3,4-dichloro-phenyl)-2-thioxo-2,3-dihydro-1H-pyrazolo[1,5-a][1,3,5]triazin-4-one
  参考文献：
  名称：

  Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II

  摘要：

  In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.063
• 作为产物：
  描述：

  2-溴-3',4'-二氯苯乙酮 在 盐酸 、 hydrazine hydrate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 3-(3,4-二氯苯基)-1H-吡唑-5-胺
  参考文献：
  名称：

  Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II

  摘要：

  In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.063

文献信息

• THERAPEUTIC COMPOUNDS AND RELATED METHODS OF USE
  申请人：Suzuki Masaki

  公开号：US20150307477A1

  公开（公告）日：2015-10-29

  Methods of treating disorders using compounds that modulate striatal-enriched tyrosine phosphatase (STEP) are described herein. Exemplary disorders include schizophrenia and cognitive deficit.

  本文描述了利用调节纹状体富集的酪氨酸磷酸酶（STEP）的化合物来治疗疾病的方法。示例疾病包括精神分裂症和认知缺陷。
• Methods of treating conditions associated with an EDG-4 receptor
  申请人：Solow-Cordero David

  公开号：US20050113283A1

  公开（公告）日：2005-05-26

  The present invention provides a method of modulating an Edg-4 receptor mediated biological activity in a cell. A cell expressing the Edg-4 receptor is contacted with a modulator of an Edg-4 receptor sufficient to modulate the Edg-4 receptor mediated biological activity. In another aspect, the present invention provides a method for modulating an Edg-4 receptor mediated biological activity in a subject. A therapeutically effective amount of a modulator of the Edg-4 receptor is administered to the subject.

  本发明提供了一种调节细胞中Edg-4受体介导的生物活性的方法。将表达Edg-4受体的细胞与足以调节Edg-4受体介导的生物活性的调节剂接触。在另一个方面，本发明提供了一种调节受体Edg-4介导的生物活性的方法。向受体施用治疗有效量的Edg-4受体调节剂。
• Aminopyrazole derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US06166038A1

  公开（公告）日：2000-12-26

  The present invention relates to a compound represented by the general formula [I]: ##STR1## wherein Ar.sup.1 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; Ar.sup.2 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; R.sup.1 and R.sup.2 may be the same or different and each represents a hydrogen atom or a lower alkyl group; R.sup.3 and R.sup.4 may be the same or different and each represents a hydrogen atom or a lower alkyl group, or R.sup.3 and R.sup.4 are linked to each other to form an alkylene group containing 2 to 4 carbon atoms which may have a lower alkyl group; and R.sup.5 represents a hydrogen atom or a lower alkyl or lower alkoxy 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.

  本发明涉及一种由通式[I]表示的化合物：##STR1##其中，Ar.sup.1代表一个芳基，可以具有来自卤素原子和低烷基和低卤代烷基群的取代基；Ar.sup.2代表一个芳基或杂环芳基，可以具有来自卤素原子和低烷基、低烯基、低卤代烷基、低烷氧基、低烷硫基、低烷基氨基、低二烷基氨基和芳基群的取代基；R.sup.1和R.sup.2可以相同或不同，每个代表氢原子或低烷基；R.sup.3和R.sup.4可以相同或不同，每个代表氢原子或低烷基，或者R.sup.3和R.sup.4连接在一起形成一个含有2到4个碳原子的烷基群，可以具有一个低烷基；R.sup.5代表氢原子或低烷基或低烷氧基，或其盐，以及一种以其为活性成分的治疗暴食症、肥胖症或糖尿病的制剂的方法。
• 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 AMINOPYRAZOLE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0945439A1

  公开（公告）日：1999-09-29

  The present invention relates to a compound represented by the general formula [I]: wherein 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 and R2 may be the same or different and each 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 lower alkyl or lower alkoxy 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]所代表的化合物： 其中Ar1代表芳基，其取代基可选自由卤素原子、低级烷基和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基组成的组；R1 和 R2 可以相同或不同，各自代表一个氢原子或一个低级烷基；R3 和 R4 可以相同或不同，各自代表一个氢原子或一个低级烷基，或 R3 和 R4 相互连接形成一个含有 2 至 4 个碳原子的亚烷基，该亚烷基可能含有一个低级烷基；以及 R5 代表一个氢原子或一个低级烷基或低级烷氧基、 或其盐，其制备方法以及治疗贪食症、肥胖症或糖尿病的药物，其活性成分均包含该物质。