(S)-benzyl 7-(2-methoxy-2-oxoethoxy)-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1223621-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-benzyl 7-(2-methoxy-2-oxoethoxy)-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS: 1223621-40-6
• 化学式: C₂₉H₃₀N₂O₆
• 分子量: 502.567
• InChiKey: PPTNJPWVZDVVOJ-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 7-(2-methoxy-2-oxoethoxy)-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 羟胺钾盐 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以23%的产率得到(S)-benzyl 7-(2-(hydroxyamino)-2-oxoethoxy)-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Design, synthesis and preliminary activity assay of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors

  摘要：

  Histone deacetylases (HDACs) are enzymes involved in tumor genesis and development. Herein, we report a novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as HDACs inhibitors. The preliminary biological screening showed that most of our compounds exhibited potent inhibitory activity against HDACs. Within this series, five compounds, 13a (IC50 = 0.58 +/- 0.10 mu M), 7d (IC50 = 1.00 +/- 0.16 mu M), 81 (IC50 = 1.06 +/- 0.14 mu M), 7i (IC50 = 1.17 +/- 0.19 mu M) and 7a (IC50 = 1.29 +/- 0.15 mu M) possessed better HDACs inhibitory activity than Vorinostat (IC50 = 1.48 +/- 0.20 mu M). So these five compounds could be used as novel lead compounds for further design of HDACs inhibitors. The anti-proliferative activities of a few compounds and the structure-activity relationships are also briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.060
• 作为产物：
  描述：

  (S)-benzyl 7-hydroxy-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以37%的产率得到(S)-benzyl 7-(2-methoxy-2-oxoethoxy)-3-(phenethylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Design, synthesis and preliminary activity assay of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors

  摘要：

  Histone deacetylases (HDACs) are enzymes involved in tumor genesis and development. Herein, we report a novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as HDACs inhibitors. The preliminary biological screening showed that most of our compounds exhibited potent inhibitory activity against HDACs. Within this series, five compounds, 13a (IC50 = 0.58 +/- 0.10 mu M), 7d (IC50 = 1.00 +/- 0.16 mu M), 81 (IC50 = 1.06 +/- 0.14 mu M), 7i (IC50 = 1.17 +/- 0.19 mu M) and 7a (IC50 = 1.29 +/- 0.15 mu M) possessed better HDACs inhibitory activity than Vorinostat (IC50 = 1.48 +/- 0.20 mu M). So these five compounds could be used as novel lead compounds for further design of HDACs inhibitors. The anti-proliferative activities of a few compounds and the structure-activity relationships are also briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.060