(4S)-5-amino-4-[[4-[3-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-iodoanilino)-8-oxopyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-5-oxopentanoic acid | 1311276-82-0

• 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: (4S)-5-amino-4-[[4-[3-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-iodoanilino)-8-oxopyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-5-oxopentanoic acid
• CAS: 1311276-82-0
• 化学式: C₃₆H₃₀IN₅O₈
• 分子量: 787.567
• InChiKey: UGYXNBOEALWHFC-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  206
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  多巴胺 、 4-(7-fluoro-6-nitro-4-oxo-4H-chromen-2-yl)benzoic acid 、 4-碘异硫氰酸苯酯 、 Fmoc-L-谷氨酸 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 (4S)-5-amino-4-[[4-[3-[2-(3,4-dihydroxyphenyl)ethyl]-2-(4-iodoanilino)-8-oxopyrano[3,2-f]benzimidazol-6-yl]benzoyl]amino]-5-oxopentanoic 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