3-(2-ethylhexyl)-N'-hydroxy-N-phenyloctanediamide | 1411986-67-8

• 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: 3-(2-ethylhexyl)-N'-hydroxy-N-phenyloctanediamide
• CAS: 1411986-67-8
• 化学式: C₂₂H₃₆N₂O₃
• 分子量: 376.539
• InChiKey: PHPVFHDMAAPRFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氧代己酸甲酯 在 溴化亚铜二甲硫醚 、 20% palladium hydroxide-activated charcoal 、 盐酸羟胺 、 氢气 、 sodium hydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 16.83h， 生成 3-(2-ethylhexyl)-N'-hydroxy-N-phenyloctanediamide
  参考文献：
  名称：

  The structural requirements of histone deacetylase inhibitors: Suberoylanilide hydroxamic acid analogs modified at the C6 position

  摘要：

  Suberoylanilide hydroxamic acid (SAHA, Vorinostat), the first FDA-approved histone deacetylase (HDAC) inhibitor drug, was modified at the C6 position to study the structural requirements for high potency and selectivity. Substituents on the C6 position only modestly influenced inhibitor potency, with poorer activity observed as substituent size increased. Interestingly, C6 substituents also modestly influenced selectivity compared to the parent compound, SAHA. This systematic study documenting the influence of substituents on the SAHA linker region will aid development of anti-cancer drugs targeting HDAC proteins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.093

文献信息

• The structural requirements of histone deacetylase inhibitors: Suberoylanilide hydroxamic acid analogs modified at the C6 position
  作者：Sun Ea Choi、Mary Kay H. Pflum

  DOI：10.1016/j.bmcl.2012.09.093

  日期：2012.12

  Suberoylanilide hydroxamic acid (SAHA, Vorinostat), the first FDA-approved histone deacetylase (HDAC) inhibitor drug, was modified at the C6 position to study the structural requirements for high potency and selectivity. Substituents on the C6 position only modestly influenced inhibitor potency, with poorer activity observed as substituent size increased. Interestingly, C6 substituents also modestly influenced selectivity compared to the parent compound, SAHA. This systematic study documenting the influence of substituents on the SAHA linker region will aid development of anti-cancer drugs targeting HDAC proteins. (C) 2012 Elsevier Ltd. All rights reserved.