1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one | 1262232-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 1-(14-methyl-11-thia-13,15-diazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(10),2,4,6,12,14,16-heptaen-16-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 1262232-27-8
• 化学式: C₂₀H₁₄N₆OS
• 分子量: 386.437
• InChiKey: QCHPYYYUHVMBOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one 在 甲醇 、 硫酸氢铵 、 氨 、 四氯化锡 、 硫脲 、 三氯氧磷 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 29.5h， 生成 4-(1-β-D-ribofuranosylsulfanyl)-1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells

  摘要：

  A series of novel substituted pyrazolo[3,4-d]pyrimidines (compounds 2-12) were synthesized starting with pyrimidinone derivative 1. Their in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cell lines has been investigated and most of the tested compounds exploited potent cytotoxic activity against MCF-7 cell lines comparable to the activity of the commonly used anticancer drug cisplatin. Treatment of MCF-7 cells with increased doses (2, 5, 10, 20 mu g/ml) of the tested compounds revealed that the activity of superoxide dismutase and the level of hydrogen peroxide were significantly increased, while the activities of catalase and glutathione peroxidase and the levels of reduced glutathione were significantly lowered compared with control MCF-7 cells. In general, acyclic nucleoside derivative 4 revealed the highest anticancer activity among the other tested compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.013
• 作为产物：
  描述：

  甲酸 、 5-amino-1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazole-4-carbonitrile 反应 5.0h， 以95%的产率得到1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  一些新型吡唑并嘧啶核苷衍生物的简便合成和抗禽流感病毒 (H5N1) 筛选

  摘要：

  5-amino-1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazole-4-的处理腈 (1) 与甲酸得到 pyrazolo[3,4-d]pyrimidin-4-one 衍生物 2. 后一种化合物的钠盐（原位生成）用一些卤代烷处理，得到相应的 N-取代化合物3-7。将甲硅烷氧基衍生物 8（也由 2 原位生成）进行核糖基化和糖基化，分别得到化合物 9 和 11。化合物 9 和 11 在甲醇氨中的脱保护分别产生游离核苷 10 和 12。此外，还测试了制备的化合物对 H5N1 病毒的抗病毒活性 [A/chicken/Egypt/1/2006]，与其他测试化合物相比，其中一些显示出中等的结果。

  DOI：

  10.1080/15257770.2010.529480

文献信息

• Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells
  作者：Aymn E. Rashad、Abeer E. Mahmoud、Mamdouh M. Ali

  DOI：10.1016/j.ejmech.2011.01.013

  日期：2011.4

  A series of novel substituted pyrazolo[3,4-d]pyrimidines (compounds 2-12) were synthesized starting with pyrimidinone derivative 1. Their in vitro cytotoxicity against human breast adenocarcinoma (MCF-7) cell lines has been investigated and most of the tested compounds exploited potent cytotoxic activity against MCF-7 cell lines comparable to the activity of the commonly used anticancer drug cisplatin. Treatment of MCF-7 cells with increased doses (2, 5, 10, 20 mu g/ml) of the tested compounds revealed that the activity of superoxide dismutase and the level of hydrogen peroxide were significantly increased, while the activities of catalase and glutathione peroxidase and the levels of reduced glutathione were significantly lowered compared with control MCF-7 cells. In general, acyclic nucleoside derivative 4 revealed the highest anticancer activity among the other tested compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.
• A Facile Synthesis and Anti-Avian Influenza Virus (H5N1) Screening of Some Novel Pyrazolopyrimidine Nucleoside Derivatives
  作者：Aymn E. Rashad、Ahmed H. Shamroukh、Randa E. Abdel-Megeid、Ahmed Mostafa、Mohamed A. Ali、Klaus Banert

  DOI：10.1080/15257770.2010.529480

  日期：2010.11.30

  latter compound (generated in situ) was treated with some alkyl halides to afford the corresponding N-substituted compounds 3–7. The siloxy derivative 8 (generated also in situ from 2) was ribosylated and glycosylated to yield compounds 9 and 11, respectively. Deprotection of compounds 9 and 11 in methanolic ammonia produced the free nucleosides 10 and 12, respectively. Moreover, the prepared compounds

  5-amino-1-(9-methyl-5,6-dihydronaphtho[1',2':4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazole-4-的处理腈 (1) 与甲酸得到 pyrazolo[3,4-d]pyrimidin-4-one 衍生物 2. 后一种化合物的钠盐（原位生成）用一些卤代烷处理，得到相应的 N-取代化合物3-7。将甲硅烷氧基衍生物 8（也由 2 原位生成）进行核糖基化和糖基化，分别得到化合物 9 和 11。化合物 9 和 11 在甲醇氨中的脱保护分别产生游离核苷 10 和 12。此外，还测试了制备的化合物对 H5N1 病毒的抗病毒活性 [A/chicken/Egypt/1/2006]，与其他测试化合物相比，其中一些显示出中等的结果。