(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)(benzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone | 1160846-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (6-hydroxy-4,7-dimethoxybenzofuran-5-yl)(benzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone
• 英文别名: (6-Hydroxy-4,7-dimethoxy-benzofuran-5-yl)-pyrimido[1,2-a]benzimidazol-3-yl-methanone；(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-pyrimido[1,2-a]benzimidazol-3-ylmethanone
• CAS: 1160846-01-4
• 化学式: C₂₁H₁₅N₃O₅
• 分子量: 389.367
• InChiKey: OJTMJJBDUDSOJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基苯并咪唑 、 4,9-Dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbaldehyde 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以65%的产率得到(6-hydroxy-4,7-dimethoxybenzofuran-5-yl)(benzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)methanone
  参考文献：
  名称：

  Synthesis of potent antitumor and antiviral benzofuran derivatives

  摘要：

  A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.069

文献信息

• Synthesis of potent antitumor and antiviral benzofuran derivatives
  作者：Shadia A. Galal、Amira S. Abd El-All、Mohamed M. Abdallah、Hoda I. El-Diwani

  DOI：10.1016/j.bmcl.2009.03.069

  日期：2009.5

  A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity. (c) 2009 Elsevier Ltd. All rights reserved.