(3S)-4-amino-3-[[4-[3-(1,3-benzodioxol-5-ylmethyl)-8-oxo-2-(propylamino)pyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-4-oxobutanoic acid | 1311276-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (3S)-4-amino-3-[[4-[3-(1,3-benzodioxol-5-ylmethyl)-8-oxo-2-(propylamino)pyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-4-oxobutanoic acid
• CAS: 1311276-77-3
• 化学式: C₃₂H₂₉N₅O₈
• 分子量: 611.611
• InChiKey: IUFFWMFQHMVNSG-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  184
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧基苄胺 、 异氰酸丙酯 、 4-(7-fluoro-6-nitro-4-oxo-4H-chromen-2-yl)benzoic acid 、 Fmoc-L-天冬氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (3S)-4-amino-3-[[4-[3-(1,3-benzodioxol-5-ylmethyl)-8-oxo-2-(propylamino)pyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-4-oxobutanoic acid
  参考文献：
  名称：

  Novel Flavonoids with Antiproliferative Activities against Breast Cancer Cells

  摘要：

  A series of flavone analogues were synthesized and evaluated for their antiproliferation activity against breast cancer cells. The IC(50) of compound 10 and 24 were determined to be at 5 mu M. These compounds were used as baits to screen breast cancer cDNA expression phage display proteome library. DNA sequencing of the binding phages suggests that eEF1A1 is a target protein for 10 and 24. Further optimization of these compounds led to the discovery of 39 with higher cytotoxic potency (IC(50) = 1 mu M) and binding to eEF1A2. Biological and biochemical data suggest that eEF1A2 might be a therapeutic target and that 39 is an excellent lead compound for further development.

  DOI：

  10.1021/jm101440r

文献信息

• Novel Flavonoids with Antiproliferative Activities against Breast Cancer Cells
  作者：Nianhuan Yao、Chao-Yu Chen、Chun-Yi Wu、Kiyomi Motonishi、Hsing-Jien Kung、Kit S. Lam

  DOI：10.1021/jm101440r

  日期：2011.7.14

  A series of flavone analogues were synthesized and evaluated for their antiproliferation activity against breast cancer cells. The IC(50) of compound 10 and 24 were determined to be at 5 mu M. These compounds were used as baits to screen breast cancer cDNA expression phage display proteome library. DNA sequencing of the binding phages suggests that eEF1A1 is a target protein for 10 and 24. Further optimization of these compounds led to the discovery of 39 with higher cytotoxic potency (IC(50) = 1 mu M) and binding to eEF1A2. Biological and biochemical data suggest that eEF1A2 might be a therapeutic target and that 39 is an excellent lead compound for further development.