(2S)-8-bromo-2-(phenylmethoxycarbonylamino)octanoic acid | 1376600-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-8-bromo-2-(phenylmethoxycarbonylamino)octanoic acid
• CAS: 1376600-38-2
• 化学式: C₁₆H₂₂BrNO₄
• 分子量: 372.259
• InChiKey: ACTUOJSYYHUWIM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-8-bromo-2-(phenylmethoxycarbonylamino)octanoic acid 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 tert-butyl (2S)-2-(phenylmethoxycarbonylamino)-8-(pyridin-2-yldisulfanyl)octanoate
  参考文献：
  名称：

  A novel series of l-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives as histone deacetylase inhibitors: Design, synthesis and molecular modeling study

  摘要：

  Histone deacetylases inhibitors (HDACIs) have become an attractive class of anticancer agents. In order to find some novel potent HDACIs, we designed and synthesized a series of L-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives. All compounds exhibited potent HDAC-inhibitory activity, and two of them had similar potency to TSA. The introduction of 2-amino-4-phenylthiazole or 9-methyleneoxy-fluorenyl group at the surface recognize domain of these HDACIs could greatly increase their HDAC-inhibitory activity. Molecular modeling studies indicated that coordination of the zinc ion by these inhibitors, and formation of hydrogen bond and hydrophobic interaction between inhibitors and HDACs were essential for the HDAC-inhibitory activities of these inhibitors. Asp181, Asp269, Leu276 and Tyr308 in the active site of HDAC2 gave favorable contributions for binding with all compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.009
• 作为产物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 、 (S)-2-amino-8-bromooctanoic acid 在 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 5.0h， 以93.2%的产率得到(2S)-8-bromo-2-(phenylmethoxycarbonylamino)octanoic acid
  参考文献：
  名称：

  A novel series of l-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives as histone deacetylase inhibitors: Design, synthesis and molecular modeling study

  摘要：

  Histone deacetylases inhibitors (HDACIs) have become an attractive class of anticancer agents. In order to find some novel potent HDACIs, we designed and synthesized a series of L-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives. All compounds exhibited potent HDAC-inhibitory activity, and two of them had similar potency to TSA. The introduction of 2-amino-4-phenylthiazole or 9-methyleneoxy-fluorenyl group at the surface recognize domain of these HDACIs could greatly increase their HDAC-inhibitory activity. Molecular modeling studies indicated that coordination of the zinc ion by these inhibitors, and formation of hydrogen bond and hydrophobic interaction between inhibitors and HDACs were essential for the HDAC-inhibitory activities of these inhibitors. Asp181, Asp269, Leu276 and Tyr308 in the active site of HDAC2 gave favorable contributions for binding with all compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.009