7-(4-nitrophenyl)-8-methyl-10-phenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-dione | 1347736-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(4-nitrophenyl)-8-methyl-10-phenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-dione
• 英文别名: 3-methyl-4-(4-nitrophenyl)-1-phenylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-dione；13-Methyl-11-(4-nitrophenyl)-15-phenyl-14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,11,13,16-heptaene-8,9-dione
• CAS: 1347736-51-9
• 化学式: C₂₇H₁₆N₄O₄
• 分子量: 460.448
• InChiKey: NAULMLDCCKHWJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 2-羟基-1,4-萘醌 、 对硝基苯甲醛 反应 0.05h， 以80%的产率得到7-(4-nitrophenyl)-8-methyl-10-phenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-dione
  参考文献：
  名称：

  Microwave induced three-component synthesis and antimycobacterial activity of benzopyrazolo[3,4-b]quinolindiones

  摘要：

  Three series of novel 4-arylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-diones 4, 7 and 9 have been efficiently obtained in good yields by three-component microwave assisted reaction between aminopyrazoles 1 or 6 (both 1-phenyl and 1-H substituted), 2-hydroxynaphthoquinone 2 and benzaldehydes 3. Compounds 4, 7 and 9 have been evaluated against fifteen Mycobacterium spp strains, and six of them have shown antimycobacterial activity. The highest inhibitory activity with MIC <= 2 mu g/mL for three of these compounds (4a, 4b and 4g) was related with their highest lipophilicity and lesser polarity within these series. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.037

文献信息

• l-Proline-catalysed sequential four-component “on water” protocol for the synthesis of structurally complex heterocyclic ortho-quinones
  作者：Stephen Michael Rajesh、Balasubramanian Devi Bala、Subbu Perumal、J. Carlos Menéndez

  DOI：10.1039/c1gc15794a

  日期：——

  The L-proline-catalyzed synthesis of 7-(aryl)-8-methyl-10-phenyl-5H-benzo[h]pyrazolo-[3,4-b]quinoline-5,6(10H)-diones via the four-component sequential reaction of phenylhydrazine, 3-aminocrotononitrile, substituted benzaldehydes and 2-hydroxynaphthalene-1,4-dione is described. This “on water” protocol proceeds in high atom economy and leads to the generation of two rings, together with two C–C, one C–N and two CN bonds in a single operation. The environmental advantages of the method include short reaction time, excellent yield, easy work-up, and the absence of extraction and chromatographic purification steps.

  本文介绍了 L-脯氨酸催化合成 7-(芳基)-8-甲基-10-苯基-5H-苯并[h]吡唑并[3,4-b]喹啉-5,6(10H)-二酮的过程，该过程通过苯肼、3-氨基巴豆腈、取代苯甲醛和 2-羟基萘-1,4-二酮的四组分顺序反应进行。这种 "水上 "方法原子经济性高，一次操作就能生成两个环，以及两个 CâC、一个 CâN 和两个 CN 键。该方法的环境优势包括反应时间短、收率高、操作简便、无需萃取和色谱纯化步骤。
• Microwave induced three-component synthesis and antimycobacterial activity of benzopyrazolo[3,4-b]quinolindiones
  作者：Jairo Quiroga、Yurina Diaz、Juan Bueno、Braulio Insuasty、Rodrigo Abonia、Alejandro Ortiz、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.ejmech.2013.12.037

  日期：2014.3

  Three series of novel 4-arylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-diones 4, 7 and 9 have been efficiently obtained in good yields by three-component microwave assisted reaction between aminopyrazoles 1 or 6 (both 1-phenyl and 1-H substituted), 2-hydroxynaphthoquinone 2 and benzaldehydes 3. Compounds 4, 7 and 9 have been evaluated against fifteen Mycobacterium spp strains, and six of them have shown antimycobacterial activity. The highest inhibitory activity with MIC <= 2 mu g/mL for three of these compounds (4a, 4b and 4g) was related with their highest lipophilicity and lesser polarity within these series. (C) 2014 Elsevier Masson SAS. All rights reserved.