3-(4,5-dihydro-5-p-tolyl-1H-pyrazol-3-yl)-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(4,5-dihydro-5-p-tolyl-1H-pyrazol-3-yl)-2H-chromen-2-one
• 英文别名: 3-[5-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-3-yl]chromen-2-one
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: JTHZYSCEWYXKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 水杨醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 bismuth(lll) trifluoromethanesulfonate 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到3-(4,5-dihydro-5-p-tolyl-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-component reaction

  摘要：

  A series of coumarin-chalcone hybrid compounds and coumarins linked to pyrazoline was synthesized in good yield and short time using a simple and efficient method. This method involved the one-pot reaction of salicylaldehyde, an alpha-ketoester and an aromatic aldehyde (in the case of the coumarin-chalcone derivatives) in addition to hydrazine hydrate (in the case of the pyrazolyl coumarins) in the presence of a catalytic amount of bismuth triflate [Bi(OTf)(3), 5 mol%]. The synthesized compounds showed scavenging activity towards the free radical 2,2-diphenyl-1-picrylhydrazyl. All compounds were characterized using IR, H-1 NMR and C-13 NMR spectroscopy. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(14)60308-9

文献信息

• A new efficient domino approach for the synthesis of coumarin-pyrazolines as antimicrobial agents targeting bacterial<scp>d</scp>-alanine-<scp>d</scp>-alanine ligase
  作者：Asha V. Chate、Ankita A. Redlawar、Giribala M. Bondle、Aniket P. Sarkate、Shailee V. Tiwari、Deepak K. Lokwani

  DOI：10.1039/c9nj00703b

  日期：——

  yields of products and column-free synthesis. The synthesized compounds were evaluated in vitro for their antimicrobial activity. Among the synthesized compounds, namely 3-(5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one (5f) was found to be the most potent D-alanine-D-alanine ligase enzyme inhibitor, with an IC50 value 106 μM, and the compound 3-(5-(p-tolyl)-4,5-dihydro-1H-p

  D-丙氨酸-D-丙氨酸连接酶（Ddl）的抑制可防止细菌的生长，这使得该酶成为紧急寻找新型有效抗菌药物的诱人且可行的靶标。在这项工作中，合成了一系列新型的香豆素连接的D-丙氨酸-D-丙氨酸连接酶吡唑啉抑制剂，并作为大肠杆菌DdlB连接酶的抑制剂进行了评估，以便使用环境友好的β-环糊精作为超分子靶向细菌的耐药菌株。催化剂通过一锅四组分合成在水中作为绿色反应介质。所有新合成的化合物均已通过元素分析和各种光谱学方法进行了表征。新方法具有值得注意的优点，包括后处理容易，反应时间短，产物的产率高和无柱合成。体外评估了合成的化合物的抗菌活性。在合成的化合物中，发现了3-（5-（4-羟基-3-甲氧基苯基）-4,5-二氢-1 H-吡唑-3-基）-2 H-色烯-2-酮（5f）是最有效的D-丙氨酸-D-丙氨酸连接酶抑制剂，IC 50值为106μM，化合物3-（5-（p -甲苯基）-4,5-二氢-1- ħ吡唑-3-基）-2-
• Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-component reaction
  作者：Mahmoud. Abd El Aleem. Ali. Ali. El-Remaily

  DOI：10.1016/s1872-2067(14)60308-9

  日期：2015.7

  A series of coumarin-chalcone hybrid compounds and coumarins linked to pyrazoline was synthesized in good yield and short time using a simple and efficient method. This method involved the one-pot reaction of salicylaldehyde, an alpha-ketoester and an aromatic aldehyde (in the case of the coumarin-chalcone derivatives) in addition to hydrazine hydrate (in the case of the pyrazolyl coumarins) in the presence of a catalytic amount of bismuth triflate [Bi(OTf)(3), 5 mol%]. The synthesized compounds showed scavenging activity towards the free radical 2,2-diphenyl-1-picrylhydrazyl. All compounds were characterized using IR, H-1 NMR and C-13 NMR spectroscopy. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.