1-benzyl 8-methyl 3-(2-ethylhexyl)octanedioate | 1411986-14-5

• 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: 1-benzyl 8-methyl 3-(2-ethylhexyl)octanedioate
• 英文别名: 1-O-benzyl 8-O-methyl 3-(2-ethylhexyl)octanedioate
• CAS: 1411986-14-5
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: WQVKAXABIPJPFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl 8-methyl 3-(2-ethylhexyl)octanedioate 在 20% palladium hydroxide-activated charcoal 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 8-ethyl-6-(2-oxo-2-(phenylamino)ethyl)dodecanoate
  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
• 作为产物：
  描述：

  6-氧代己酸甲酯 在 溴化亚铜二甲硫醚 、 sodium hydride 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 4.83h， 生成 1-benzyl 8-methyl 3-(2-ethylhexyl)octanedioate
  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.