2-phenyl-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid | 1017082-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-phenyl-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid
• 英文别名: 7-(4-Fluorophenyl)-2-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylic acid
• CAS: 1017082-08-4
• 化学式: C₁₉H₁₂FN₃O₂
• 分子量: 333.322
• InChiKey: BMCSTZURHDUSPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基苯并噻唑 、 2-phenyl-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 以81%的产率得到N-(6-methoxybenzo[d]thiazol-2-yl)-2-phenyl-7-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Synthesis of pyrazolo[1,5-a]pyrimidine linked aminobenzothiazole conjugates as potential anticancer agents

  摘要：

  A series of pyrazolo[1,5-a]pyrimidine linked 2-aminobenzothizole conjugates (6a-t) were synthesized and evaluated for their anticancer activity against five human cancer cell lines. Among them two compounds 6p and 6m showed significant anticancer activity with IC50 values ranging from 2.01 to 7.07 and 1.94-3.46 mu M, respectively. Moreover, cell cycle arrest in G2/M and reduction in Cdk1 expression level were observed upon treatment of these compounds and they also induced caspase-3 dependent apoptosis. This was further confirmed by staining as well as DNA fragmentation analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.129
• 作为产物：
  描述：

  4-(4-氟苯基)-2,4-二氧代丁酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 2-phenyl-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  通过雌激素信号传导调节MCF-7细胞增殖的2-苯胺基烟酰-吡唑并[1,5- a ]嘧啶共轭物的合成及其机理

  摘要：

  合成了一系列的壬基烟酰胺基连接的吡唑并[1,5- a ]嘧啶共轭物（6a – x），并评估了它们的抗增殖活性。这些缀合物中的一些在MCF-7细胞系中显示出有希望的细胞毒性作用，并且在这些6a和6c中，除了G2 / M细胞周期停滞外，还显示出显着的作用。有趣的是，它们对调节乳腺癌细胞增殖的cyclin D1，Bcl-2和survivin蛋白显示出深远的影响。此外，研究了ERα蛋白的表达，以了解这些偶联物在雌激素阳性乳腺癌细胞（如MCF-7和化合物6a和6c）中对雌激素活性的调节作用。 减少了他们的活动。

  DOI：

  10.1016/j.bmcl.2016.02.072

文献信息

• Synthesis of pyrazolo[1,5-a]pyrimidine linked aminobenzothiazole conjugates as potential anticancer agents
  作者：Ahmed Kamal、Jaki R. Tamboli、V. Lakshma Nayak、S.F. Adil、M.V.P.S. Vishnuvardhan、S. Ramakrishna

  DOI：10.1016/j.bmcl.2013.03.129

  日期：2013.6

  A series of pyrazolo[1,5-a]pyrimidine linked 2-aminobenzothizole conjugates (6a-t) were synthesized and evaluated for their anticancer activity against five human cancer cell lines. Among them two compounds 6p and 6m showed significant anticancer activity with IC50 values ranging from 2.01 to 7.07 and 1.94-3.46 mu M, respectively. Moreover, cell cycle arrest in G2/M and reduction in Cdk1 expression level were observed upon treatment of these compounds and they also induced caspase-3 dependent apoptosis. This was further confirmed by staining as well as DNA fragmentation analysis. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and mechanistic aspects of 2-anilinonicotinyl-pyrazolo[1,5-a]pyrimidine conjugates that regulate cell proliferation in MCF-7 cells via estrogen signaling
  作者：Ahmed Kamal、Shaikh Faazil、S.M. Ali Hussaini、M. Janaki Ramaiah、M. Balakrishna、Nibedita Patel、S.N.C.V.L. Pushpavalli、Manika Pal-Bhadra

  DOI：10.1016/j.bmcl.2016.02.072

  日期：2016.4

  pyrazolo[1,5-a]pyrimidine conjugates (6a–x) were synthesized and evaluated for their antiproliferative activity. Some of these conjugates exhibited promising cytotoxic effects in the MCF-7 cell line and among these 6a and 6c exhibited significant effects, apart from G2/M cell cycle arrest. Interestingly they showed profound effects on cyclin D1, Bcl-2 and survivin proteins that regulate breast cancer cell

  合成了一系列的壬基烟酰胺基连接的吡唑并[1,5- a ]嘧啶共轭物（6a – x），并评估了它们的抗增殖活性。这些缀合物中的一些在MCF-7细胞系中显示出有希望的细胞毒性作用，并且在这些6a和6c中，除了G2 / M细胞周期停滞外，还显示出显着的作用。有趣的是，它们对调节乳腺癌细胞增殖的cyclin D1，Bcl-2和survivin蛋白显示出深远的影响。此外，研究了ERα蛋白的表达，以了解这些偶联物在雌激素阳性乳腺癌细胞（如MCF-7和化合物6a和6c）中对雌激素活性的调节作用。 减少了他们的活动。