(S)-tert-butyl 3-(tert-butylcarbamoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1223621-10-0

• 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)-tert-butyl 3-(tert-butylcarbamoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• 英文别名: tert-butyl (3S)-3-(tert-butylcarbamoyl)-7-[2-(hydroxyamino)-2-oxoethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1223621-10-0
• 化学式: C₂₁H₃₁N₃O₆
• 分子量: 421.494
• InChiKey: FDOJSPRQHBBJDF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 3-(tert-butylcarbamoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以93%的产率得到(S)-N-tert-butyl-7-(2-(hydroxyamino)-2-oxoethoxy)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide hydrochloride
  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)-tert-butyl 3-(tert-butylcarbamoyl)-7-(2-methoxy-2-oxoethoxy)-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28%的产率得到(S)-tert-butyl 3-(tert-butylcarbamoyl)-7-(2-(hydroxyamino)-2-oxoethoxy)-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