3-(2-氯苯基)-1H-1,2,4-三唑-5-胺 | 54463-89-7

• 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-(2-氯苯基)-1H-1,2,4-三唑-5-胺
• 英文名称: 3-amine-5-(2-chlorophenyl)-4H-1,2,4-triazol
• 英文别名: 5-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine；5-(2-chlorophenyl)-1H-1,2,4-triazol-3-amine
• CAS: 54463-89-7
• 化学式: C₈H₇ClN₄
• 分子量: 194.623
• InChiKey: LVSNWMVOAUEVKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3-(2-氯苯基)-1H-1,2,4-三唑-5-胺 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(2-chlorophenyl)-5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
  参考文献：
  名称：

  Synthesis, anti-thymidine phosphorylase activity and molecular docking of 5-thioxo-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ones

  摘要：

  In our lead finding program, a series of 5-thioxo-[1,2,4] triazolo[1,5-a][1,3,5]triazin-7-ones and their 5-thio- alkyl derivatives were designed and synthesized which contained different substituents at ortho-position of 2-phenyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the synthesized compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase (TP), comparable to reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). The study also inferred that the ortho-substituted group at the phenyl ring and 5-thio-alkyl moiety imparted steric hindrance effects in the binding site of the enzyme, leading to a reduced inhibitory response. In addition, compound 3a was identified as a mixed-type inhibitor of TP. Moreover, computational docking study was performed to illustrate the important structural information on the plausible ligand-enzyme binding interactions. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.07.004
• 作为产物：
  描述：

  2-氯苯甲酸甲酯 在 对甲苯磺酸 、 一水合肼 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 3-(2-氯苯基)-1H-1,2,4-三唑-5-胺
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of tricyclic derivatives as selective RXFP4 agonists

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104782
• 作为试剂：
  描述：

  2-(2-chlorobenzoyl)hydrazinecarboximidamide 在 水 、 3-(2-氯苯基)-1H-1,2,4-三唑-5-胺 作用下， 以 水 为溶剂， 反应 4.0h， 以This resulted in 1.5 g (55%) of 3-(2-chlorophenyl)-1H-1,2,4-triazol-5-amine as a yellow oil的产率得到3-(2-氯苯基)-1H-1,2,4-三唑-5-胺
  参考文献：
  名称：

  Heterocyclic compounds for the inhibition of PASK

  摘要：

  本文披露了新的杂环化合物和组合物及其作为药物治疗疾病的应用。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，以治疗诸如糖尿病等疾病。

  公开号：

  US09278973B2

文献信息

• [EN] HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES POUR L'INHIBITION DE PASK
  申请人：BIOENERGENIX

  公开号：WO2014066743A1

  公开（公告）日：2014-05-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• A novel multicomponent microwave-assisted synthesis of 5-aza-adenines
  作者：Anton V. Dolzhenko、Svetlana A. Kalinina、Dmitrii V. Kalinin

  DOI：10.1039/c3ra41932k

  日期：——

  A novel multicomponent strategy for the efficient synthesis of 5-aza-adenines was developed. 5-Aza-adenines were prepared in a one-pot fashion from 5-amino-1,2,4-triazoles, cyanamide and triethyl orthoformate under microwave irradiation. The operational simplicity, efficiency and accessibility of this method make it highly attractive for the generation of bioactive compound libraries.

  开发了一种新型多组分策略，用于高效合成5-偶氮腺嘌呤。通过微波照射下，以5-氨基-1,2,4-三氮唑、氰脲酰胺和三乙基原甲酸酯在单一容器中制备了5-偶氮腺嘌呤。该方法操作简便、高效且易于实施，使其在生成生物活性化合物库方面极具吸引力。
• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：BioEnergenix LLC

  公开号：US20160235755A1

  公开（公告）日：2016-08-18

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为治疗疾病的药物的应用。还提供了抑制人或动物体内PAS激酶（PASK）活性的方法，以治疗糖尿病等疾病。
• 一类取代三环结构的化合物、其制备方法及用途
  申请人：中国科学院上海药物研究所

  公开号：CN112745319B

  公开（公告）日：2022-06-17

  本发明涉及下式I所示的一类取代三环结构的化合物、其制备方法和用途。所述化合物可以用于制备松弛素/胰岛素样家族肽受体4调节剂，以及用于制备预防或治疗代谢性疾病的药物。
• TRIAZOLE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0710654A1

  公开（公告）日：1996-05-08

  An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) or the following formula (III) wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.

  一种预防和治疗免疫相关疾病的制剂，特别是免疫抑制剂，一种预防和治疗过敏性疾病的制剂，一种预防和治疗嗜酸性粒细胞相关疾病的制剂和一种嗜酸性粒细胞增多抑制剂，其活性成分包括下式（I）的一系列三唑衍生物 或下式（III） 其中各符号如说明书中所定义，或其药学上可接受的盐。一种新型单环或双环三唑衍生物。本发明的预防和治疗免疫相关疾病的制剂，特别是免疫抑制剂、预防和治疗过敏性疾病的制剂、预防和治疗嗜酸性粒细胞相关疾病的制剂、嗜酸性粒细胞抑制剂和新型三唑衍生物都具有优异的嗜酸性粒细胞抑制作用和淋巴细胞活化抑制作用。它们毒性低，作用持久。它们对治疗嗜酸性粒细胞和淋巴细胞的积聚和活化、呼吸道炎症性疾病、嗜酸性粒细胞相关疾病（如嗜酸性粒细胞增多症）以及免疫相关疾病特别有效。