3-(5-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one | 1148141-49-4

• 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-(5-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one
• 英文别名: 3-[3-(4-Hydroxyphenyl)-2-phenyl-3,4-dihydropyrazol-5-yl]chromen-2-one
• CAS: 1148141-49-4
• 化学式: C₂₄H₁₈N₂O₃
• 分子量: 382.419
• InChiKey: GNCCEJHCMKUIHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 3-(5-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one
  参考文献：
  名称：

  Antioxidant effectiveness generated by one or two phenolic hydroxyl groups in coumarin-substituted dihydropyrazoles

  摘要：

  A cascade operation was designed to synthesize nine coumarin-substituted dihydropyrazoles with only one or two phenolic hydroxyl groups contained. Antioxidant abilities of the obtained compounds were evaluated by inhibiting 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu2+/glutathione (GSH)-, and center dot OH-induced oxidation of DNA. It was found that less phenolic hydroxyl groups can enhance the abilities of coumarin-substituted dihydropyrazoles to protect DNA against the oxidation. Moreover, these coumarin-substituted dihydropyrazoles were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6sulfonate) cationic radical (ABTS(+.)), 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that double phenolic hydroxyl groups were more beneficial for enhancing the abilities of coumarin-substituted dihydropyrazoles to quench the aforementioned radicals. Therefore, dihydropyrazole linked with coumarin exhibited powerful antioxidant effectiveness even in the case of less phenolic hydroxyl groups involved. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.059

文献信息

• Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents
  作者：Suresh Khode、Veeresh Maddi、Prashant Aragade、Mahesh Palkar、Pradeep Kumar Ronad、Shivalingarao Mamledesai、A.H.M. Thippeswamy、D. Satyanarayana

  DOI：10.1016/j.ejmech.2008.09.020

  日期：2009.4

  A novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines (3a–l) were synthesized by reacting various substituted 3-aryl-1-(3-coumarinyl)propan-1-ones (2a–l) with phenylhydrazine in the presence of hot pyridine. Structures of all new synthesized compounds were characterized on the basis of elemental analysis and spectral data (IR, 1H NMR and 13C NMR). The title compounds were screened

  通过使各种取代的3-芳基-1-（3-香豆基）丙烷反应，合成了一系列新的5-（取代）芳基-3-（3-香豆基）-1-苯基-2-吡唑啉（3a - l）。在热吡啶存在下与苯肼形成1-ones（2a – l）。根据元素分析和光谱数据（IR，1 H NMR和13 C NMR）对所有新合成化合物的结构进行表征。以12 mg制备的化合物中的化合物3d，e，i和j为原料，以200 mg / kg bw的剂量筛选标题化合物的体内抗炎和镇痛活性。在角叉菜胶诱导的大鼠水肿爪等急性炎症模型中显示出显着的抗炎活性，而在3D辅助佐剂诱发的关节炎等慢性炎症模型中，化合物3d和e显示出显着的活性，并与双氯芬酸（13.5 mg / kg bw）进行了比较作为标准药物。还发现这些化合物在乙酸诱导的扭体模型中具有显着的镇痛活性，在酵母诱导的发热模型中具有最小的致溃疡指数，具有解热活性。
• 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-