3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-amine | 1196908-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-amine
• 英文别名: 5-(4-Methoxyphenyl)-2-phenyl-1,2,4-triazol-3-amine；5-(4-methoxyphenyl)-2-phenyl-1,2,4-triazol-3-amine
• CAS: 1196908-53-8
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: AUVMPOWRGRMNLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-amine 在 tetrakis(acetonitrile)copper(I) perchlorate 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Copper salt-catalyzed formation of a novel series of triazole–spirodienone conjugates with potent anticancer activity

  摘要：

  铜盐催化的氧化胺化反应导致形成了一系列新型的三唑-螺二烯酮共轭物，即4-三唑基-1-氧杂-4-氮杂螺[4,5]癸-6,9-二烯-3,8-二酮和4-三唑基-1-氧杂-4-氮杂螺[4,5]癸-6,9-二烯-8-酮。

  DOI：

  10.1039/c6ra24764d
• 作为产物：
  描述：

  P-甲氧基苯甲酸2-苯基酰肼 在 五氯化磷 作用下， 以 三氯氧磷 为溶剂， 反应 6.33h， 生成 3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-amine
  参考文献：
  名称：

  1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies

  摘要：

  The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2-15). This study produced some interesting compounds endowed with good hA(3) receptor affinity and selectivity. In addition, to find new insights about the structural requirements for hA(3) receptor-ligand interaction, the tricyclic TQX ring was destroyed yielding some 1,2,4-triazole derivatives (compounds 16-23). These simplified compounds, though maintaining the crucial structural requirements for adenosine receptor-ligand interaction, have a very low hA(3) adenosine receptor affinity, the only exception being compound 23 (1-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]-3-phenylurea) endowed with a K-i value in the micro-molar range and high hA(3) selectivity versus both hA(1) and hA(2A) AR subtypes. Evaluation of the side products obtained in the herein reported synthetic pathways led to the identification of some new triazolo[1,5-a]quinoxalines as hA(3)AR antagonists (compounds 24-27). These derivatives, though lacking the classical structural requirements for the anchoring at the hA(3) receptor site, show high hA(3) affinity and in some case selectivity versus hA(1) and hA(2A) subtypes. Molecular docking of the herein reported tricyclic and simplified derivatives was carried out to depict their hypothetical binding mode to our model of hA(3) receptor. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.033

文献信息

• Highly Efficient Cyanoimidation of Aldehydes
  作者：Ping Yin、Wen-Bo Ma、Yue Chen、Wen-Cai Huang、Yong Deng、Ling He

  DOI：10.1021/ol902207h

  日期：2009.12.3

  Cyanoimidation of aldehydes using cyanamide as a nitrogen source and using NBS as an oxidant was achieved in high yields without the addition of a catalyst. The method has several advantages, including mild conditions, simple workflow, and inexpensive reagents. The reaction proceeds in a one-pot manner, giving rise to the formation of intermolecular C−N and C−O bonds. Subsequently, the substituted

  使用氰酰胺作为氮源并使用NBS作为氧化剂对醛进行氰化酰亚胺化反应，无需添加催化剂即可实现高收率。该方法具有许多优点，包括条件温和，工作流程简单和试剂便宜。反应以一锅法方式进行，从而导致形成分子间的C N和C O键。随后，取代的N-氰基亚氨基甲酸酯产物也可以进行环化反应，以高收率得到1,2,4-三唑衍生物。
• From Dinitrogen to N‐Containing Organic Compounds: Using Li ₂ CN ₂ as a Synthon
  作者：Li‐Jun Wu、Qianru Wang、Jianping Guo、Junnian Wei、Ping Chen、Zhenfeng Xi

  DOI：10.1002/anie.202219298

  日期：——

  A strategy for the conversion of inert N2 into various nitrogen-containing organic compounds is presented. The activated N-containing species Li2CN2 is successfully prepared in high yields from N2 gas, C and LiH. Li2CN2 can be transformed into a range of N-containing organic compounds, including cyanamides, carbodiimides, N-aryl cyanamides and 1,2,4-triazole derivatives. 15N-labeled products, including

  介绍了一种将惰性 N 2转化为各种含氮有机化合物的策略。活性含氮物质Li 2 CN 2成功地从N 2气体、C和LiH中以高产率制备。Li 2 CN 2可以转化为一系列含氮有机化合物，包括氰胺、碳二亚胺、N-芳基氰胺和1,2,4-三唑衍生物。还从15 N 2气体制备了 15 N-标记的产物，包括恶唑烷衍生物。
• 1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure–affinity relationships and molecular modeling studies
  作者：Daniela Catarzi、Flavia Varano、Daniela Poli、Lucia Squarcialupi、Marco Betti、Letizia Trincavelli、Claudia Martini、Diego Dal Ben、Ajiroghene Thomas、Rosaria Volpini、Vittoria Colotta

  DOI：10.1016/j.bmc.2014.11.033

  日期：2015.1

  The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2-15). This study produced some interesting compounds endowed with good hA(3) receptor affinity and selectivity. In addition, to find new insights about the structural requirements for hA(3) receptor-ligand interaction, the tricyclic TQX ring was destroyed yielding some 1,2,4-triazole derivatives (compounds 16-23). These simplified compounds, though maintaining the crucial structural requirements for adenosine receptor-ligand interaction, have a very low hA(3) adenosine receptor affinity, the only exception being compound 23 (1-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]-3-phenylurea) endowed with a K-i value in the micro-molar range and high hA(3) selectivity versus both hA(1) and hA(2A) AR subtypes. Evaluation of the side products obtained in the herein reported synthetic pathways led to the identification of some new triazolo[1,5-a]quinoxalines as hA(3)AR antagonists (compounds 24-27). These derivatives, though lacking the classical structural requirements for the anchoring at the hA(3) receptor site, show high hA(3) affinity and in some case selectivity versus hA(1) and hA(2A) subtypes. Molecular docking of the herein reported tricyclic and simplified derivatives was carried out to depict their hypothetical binding mode to our model of hA(3) receptor. (C) 2014 Elsevier Ltd. All rights reserved.
• Copper salt-catalyzed formation of a novel series of triazole–spirodienone conjugates with potent anticancer activity
  作者：Linghui Gu、Peng Wang、Qiu Zhong、Yuxing Deng、Jiangping Xie、Fei Liu、Fan Xiao、Shilong Zheng、Yue Chen、Guangdi Wang、Ling He

  DOI：10.1039/c6ra24764d

  日期：——

  Copper salt-catalyzed oxidative amination resulted in the formation of a novel series of triazole–spirodienone conjugates, 4-triazolyl-1-oxa-4-azaspiro[4,5]deca-6,9-dien-3,8-diones and 4-triazolyl-1-oxa-4-azaspiro[4,5]deca-6,9-dien-8-ones.

  铜盐催化的氧化胺化反应导致形成了一系列新型的三唑-螺二烯酮共轭物，即4-三唑基-1-氧杂-4-氮杂螺[4,5]癸-6,9-二烯-3,8-二酮和4-三唑基-1-氧杂-4-氮杂螺[4,5]癸-6,9-二烯-8-酮。