1-(2-氯苯基)-1H-1,2,3-三唑-4-羧酸 | 1038261-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-氯苯基)-1H-1,2,3-三唑-4-羧酸
• 英文名称: 1-(2-chlorophenyl)-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 1-(2-chlorophenyl)triazole-4-carboxylic acid
• CAS: 1038261-38-9
• 化学式: C₉H₆ClN₃O₂
• mdl: MFCD11168140
• 分子量: 223.619
• InChiKey: KFXPXGBVJANHQI-UHFFFAOYSA-N

物化性质

• 沸点：
  463.9±51.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-氯苯基)-1H-1,2,3-三唑-4-羧酸 在 potassium pyrosulfate 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 1-(2-氯苯基)三唑
  参考文献：
  名称：

  炔丙醇一锅法合成1-单取代1,2,3-三唑

  摘要：

  实现了由炔丙醇和各种芳基叠氮化物一锅法合成 1-单取代-1,2,3-三唑。这种简单的方法通过三步一锅法以良好到极好的收率提供了对各种 1-单取代 1,2,3-三唑衍生物的简洁有效的访问。

  DOI：

  10.1055/s-0036-1589157
• 作为产物：
  描述：

  1-(2-chlorophenyl)-1H-1,2,3-triazole-4-carbonitrile 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以93.5%的产率得到1-(2-氯苯基)-1H-1,2,3-三唑-4-羧酸
  参考文献：
  名称：

  Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors

  摘要：

  A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.035

文献信息

• Boronic Acid Catalysis for Mild and Selective [3+2] Dipolar Cycloadditions to Unsaturated Carboxylic Acids
  作者：Hongchao Zheng、Robert McDonald、Dennis G. Hall

  DOI：10.1002/chem.200903484

  日期：2010.5.10

  activation of unsaturated carboxylic acids is applied in several classic dipolar [3+2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can

  在本文中，用于不饱和羧酸活化的硼酸催化（BAC）的概念被应用在几种经典的偶极[3 + 2]环加成中，涉及叠氮化物，腈氧化物和硝酮作为伙伴。这些环加成物可用于生产药学上感兴趣的小的杂环产物，例如三唑，异恶唑和异恶唑烷。这些环加合物是直接形成的，并且包括可以用于进一步转化的游离羧酸官能度，从而避免了事先的掩蔽或官能化。在所有情况下，BAC都能在较温和的条件下提供更快的反应，并大大提高了产品收率和区域选择性。在某些情况下，例如叠氮化物与2-链烷酸反应生成三唑，邻位催化使用热活化时，硝基苯硼酸可避免不良的产物脱羧反应。通过使用NMR光谱研究，表明硼酸催化剂可以通过不饱和羧酸中的LUMO降低作用来提供活化作用，这很可能是通过单酰化的半硼酸酯中间体造成的。
• Synthesis of 1,2,3-triazole hydrazide derivatives exhibiting anti-phytopathogenic activity
  作者：Xing Wang、Zhi-Cheng Dai、Yong-Fei Chen、Ling-Ling Cao、Wei Yan、Sheng-Kun Li、Jian-Xin Wang、Zheng-Guang Zhang、Yong-Hao Ye

  DOI：10.1016/j.ejmech.2016.10.006

  日期：2017.1

  A series of new 1,2,3-triazole derivatives have been prepared and screened for their antifungal activity against phytopathogenic fungi using the mycelium growth inhibition method in vitro. The results indicated that the 1,2,3-triazole hydrazide scaffold displayed significant antifungal activity. Compound 6ad exhibited the most potent anti-phytopathogenic activity, with EC50 values of 0.18, 0.35, 0

  制备了一系列新的1,2,3-三唑衍生物，并通过体外抑制菌丝生长的方法筛选了它们对植物病原真菌的抑菌活性。结果表明1,2,3-三唑酰肼支架显示出显着的抗真菌活性。化合物6ad表现出最有效的抗植物病原活性，其对茄根毛霉菌，菌核盘菌，禾谷镰刀菌和稻瘟病菌的EC 50值分别为0.18、0.35、0.37和2.25μgmL -1。体内测试表明6ad对控制由上述植物病原体引起的稻鞘枯萎病，油菜菌核腐烂病，镰刀菌枯萎病和稻瘟病有效。这项工作表明，1,2,3-三唑和酰肼部分的组合在将来可能是很有前途的杀真菌剂支架。
• Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors
  作者：Mingmei Liu、Yunlei Hou、Weile Yin、Shunguang Zhou、Ping Qian、Zhuang Guo、Liying Xu、Yangfang Zhao

  DOI：10.1016/j.ejmech.2016.04.035

  日期：2016.8

  A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity. (C) 2016 Elsevier Masson SAS. All rights reserved.
• One-Pot Synthesis of 1-Monosubstituted 1,2,3-Triazoles from Propargyl Alcohol
  作者：Zhen Chen、Chunmei Han、Suping Dong、Wensheng Zhang

  DOI：10.1055/s-0036-1589157

  日期：2018.3

  A one-pot synthesis of 1-monosubstituted-1,2,3-triazoles from propargyl alcohol and various aryl azides was achieved. This simple method provides concise and efficient access to various 1-monosubstituted 1,2,3-triazole derivatives through a three-step one-pot ­sequence in good to excellent yields.

  实现了由炔丙醇和各种芳基叠氮化物一锅法合成 1-单取代-1,2,3-三唑。这种简单的方法通过三步一锅法以良好到极好的收率提供了对各种 1-单取代 1,2,3-三唑衍生物的简洁有效的访问。