7-(3,4-dimethoxyphenyl)-N-(6-fluorobenz[d]thiazol-2-yl)-2-phenylpyrazolo[1,5-a]pyri midine-5-carboxamide | 1437792-21-6

• 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: 7-(3,4-dimethoxyphenyl)-N-(6-fluorobenz[d]thiazol-2-yl)-2-phenylpyrazolo[1,5-a]pyri midine-5-carboxamide
• 英文别名: 7-(3,4-dimethoxyphenyl)-N-(6-fluoro-1,3-benzothiazol-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidine-5-carboxamide
• CAS: 1437792-21-6
• 化学式: C₂₈H₂₀FN₅O₃S
• 分子量: 525.563
• InChiKey: VQYUJMSZTBDGQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 7-(4-methoxyphenyl)-2-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylate 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 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 7-(3,4-dimethoxyphenyl)-N-(6-fluorobenz[d]thiazol-2-yl)-2-phenylpyrazolo[1,5-a]pyri midine-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

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.