1,5-dihydro-3,5-dimethyl-1-phenyl-4H-pyrazolo[4,3-c]quinolin-4-one | 71814-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-dihydro-3,5-dimethyl-1-phenyl-4H-pyrazolo[4,3-c]quinolin-4-one
• 英文别名: 3,5-dimethyl-1-phenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one；3,5-dimethyl-N-phenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one；3,5-dimethyl-1-phenyl-1,5-dihydro-4Hpyrazolo[4,3-c]quinolin-4-one；3,5-dimethyl-1-phenyl-1H-pyrazolo[4,3-c]quinolin-4(5H)-one；3,5-dimethyl-1-phenyl-1,5-dihydro-pyrazolo[4,3-c]quinolin-4-one；N,3-Dimethyl-5-phenyl-pyrazolo<4.5-c>carbostyril；3,5-Dimethyl-1-phenylpyrazolo[4,3-c]quinolin-4-one
• CAS: 71814-52-3
• 化学式: C₁₈H₁₅N₃O
• 分子量: 289.337
• InChiKey: ZREGNNKOZSTGKI-UHFFFAOYSA-N

物化性质

• 熔点：
  190-193 °C(Solv: ligroine (8032-32-4))
• 沸点：
  515.3±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  sodium 1-methyl-2-oxo-3-[1-(phenylhydrazono)ethyl]-1,2-dihydroquinolin-4-olate 以 氯苯 、 乙腈 为溶剂， 反应 5.0h， 生成 1,5-dihydro-3,5-dimethyl-1-phenyl-4H-pyrazolo[4,3-c]quinolin-4-one
  参考文献：
  名称：

  Stadlbauer, Wolfgang; Hojas, Gerhard, Journal of Heterocyclic Chemistry, 2004, vol. 41, # 5, p. 681 - 690

  摘要：

  DOI：

文献信息

• Synthesis and antioxidant properties of some novel 1,3,4,2-oxadiazaphosphepino[6,7-<i>c</i>]quinolinones and pyrazolo[3,4:4′,3′]quinolino[5,1-<i>c</i>][1,4,2]oxazaphosphinine
  作者：Mohamed M. Hassan、Somaia M. Abdel-Kariem、Tarik E. Ali

  DOI：10.1080/10426507.2017.1290625

  日期：2017.7.3

  and phenyl phosphonic dichloride, respectively, in dry dioxane. Also, reaction of hydrazone 2 with tris(2-chloroethyl)phosphite under the same reaction conditions gave pyrazolo[3,4:4′,3′]quinolino[5,1-c][1,4,2]oxazaphosphinine 10. However, when hydrazone 2 was treated with phosphonic acid, phosphorus tribromide or phosphorus oxychloride, 3,5-dimethyl-1-phenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one

  图形摘要 摘要 一系列新型 1,3,4,2-oxadiazaphosphepino[6,7-c]quinolinones 3–5, 9, 和 11 已通过处理 4-hydroxy-1-methyl-3-[1 -(2-苯肼基)乙基]喹啉-2(1H)-一 (2) 与一些硫化磷、亚磷酸二乙酯和苯基膦酰二氯，分别在干燥二恶烷中。此外，腙2与亚磷酸三(2-氯乙基)酯在相同反应条件下反应得到吡唑并[3,4:4',3']喹啉[5,1-c][1,4,2]氧氮杂膦10。然而，当腙 2 用膦酸、三溴化磷或三氯氧化磷处理时，3,5-二甲基-1-苯基-1,5-二氢-4H-吡唑并[4,3-c]喹啉-4-酮（7 ) 在所有情况下都被隔离。评价化合物的抗氧化活性。在合成的化合物中，1,3,4,2-oxadiazaphosphepino[6,
• Synthesis of Pyrazolo[4,3-<i>c</i>]quinolin-4-ones and Indolo[3,2-<i>c</i>]quinolin-6-ones by the Photocyclization of <i>N</i>-Aryl-<i>o</i>-chloroheteroarenecarboxamides
  作者：Wei Zhang、Shenci Lu、Jinhui Pan、Jie Zhang

  DOI：10.1055/s-2008-1067013

  日期：2008.5

  An efficient synthesis of pyrazolo[4,3- C]quinolin-4-ones and indolo[3,2- C]quinolin-6-ones has been achieved by the photocyclization of 5-chloro- N-phenyl-1 H-pyrazole-4-carboxamides and 2-chloro- N-phenyl-1 H-indole-3-carboxamides in acetone.

  5-氯-N-苯基-1 H-吡唑光环化高效合成吡唑并[4,3-C]喹啉-4-酮和吲哚[3,2-C]喹啉-6-酮丙酮中的 -4-羧酰胺和 2-氯-N-苯基-1 H-吲哚-3-羧酰胺。
• Pyrazolo[4,5-c]quinolines. Synthesis and specific inhibition of benzodiazepine receptor binding
  作者：Fabrizio Melani、Lucia Cecchi、Giovanna Palazzino、Guido Filacchioni、Claudia Martini、Emanuela Pennacchi、Antonio Lucacchini

  DOI：10.1021/jm00152a019

  日期：1986.2

  for their ability to displace specific [3H]flunitrazepam binding from bovine brain membranes. The 5-N-methyl derivatives 2a-c,e were the compounds that bound with the highest affinity within this class. The replacement of the carbonyl group with other substituents and the resulting aromatization of the pyridine moiety greatly decreased the binding affinity. From a Lineweaver-Burk analysis on the most

  一系列的1-芳基-3,5-二甲基-4,5-二氢-1H-吡唑并[4,5-c]喹啉-4-酮（2a-e）和1-芳基-3-甲基-1H-制备在第4位带有不同取代基的吡唑并[4,5-c]喹啉（3-7a-e），并测试其取代牛脑膜上特定[3H]氟硝西m结合的能力。5-N-甲基衍生物2a-c，e是此类中具有最高亲和力的化合物。用其他取代基取代羰基并导致吡啶部分的芳构化大大降低了结合亲和力。根据对最活性化合物2b的Lineweaver-Burk分析，似乎抑制作用是竞争性的。
• Object-oriented synthetic approach toward angular and linear fused pyrazoloquinolines of biological importance with InCl₃catalyst
  作者：Thangaraj Arasakumar、Sadasivam Mathusalini、Krishnasamy Lakshmi、Palathurai Subramaniam Mohan、Athar Ata、Chia-Her Lin

  DOI：10.1080/00397911.2015.1133827

  日期：2016.2

  A simple and short approach for the synthesis of pyrazolo[3,4-b]quinoline (3a-3p) and pyrazolo[4,3-c]quinoline (6a-6h) using various Lewis acid catalysts was developed. InCl3 was found to be more effective in providing greater yield of products compared to Yb(OTf)(3), Sc(OTf)(3), SnCl4, AlCl3, TiCl4, ZnCl2, FeCl3, and BF3 center dot Et2O. Moreover, a comparison of conventional and microwave methods has revealed that the latter method is more efficient compared to former one. Structures were confirmed by Fourier transform infrared, mass spectrometry, H-1 and C-13 NMR, X-ray crystallography, and elemental analyses. All of the synthesized compounds were evaluated for alpha-glucosidase inhibitory activity. Compounds 3a, 3p, 3i, 3h, 3k, 3o, and 3g exhibited anti alpha-glucosidase inhibitory activity with IC50 values of 57.5, 60.3, 65.9, 71.9, 80.8, 123.7, and 126.4 mu M, respectively, which is quite comparable to the standard drug acarbose (IC50=115.8 mu M).
• 10.3998/ark.5550190.0015.407
  作者：Daidone, Giuseppe、Maggio, Benedetta、Raffa, Demetrio、Meneghetti, Fiorella

  DOI：10.3998/ark.5550190.0015.407

  日期：——