6-[(methoxymethylphosphinyl)oxy]-N-phenylhexaneamide | 606092-25-5

• 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: 6-[(methoxymethylphosphinyl)oxy]-N-phenylhexaneamide
• 英文别名: 6-[methoxy(methyl)phosphoryl]oxy-N-phenylhexanamide
• CAS: 606092-25-5
• 化学式: C₁₄H₂₂NO₄P
• 分子量: 299.307
• InChiKey: GFONOAAQSUYIEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-[(methoxymethylphosphinyl)oxy]-N-phenylhexaneamide 在 lithium hydroxide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 lithium;(6-anilino-6-oxohexoxy)-methylphosphinate
  参考文献：
  名称：

  Phosphorus-Based SAHA Analogues as Histone Deacetylase Inhibitors

  摘要：

  graphicThree analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Anti proliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

  DOI：

  10.1021/ol035056n
• 作为产物：
  描述：

  甲基脂肪酰氯 在 lithium aluminium tetrahydride 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 6-[(methoxymethylphosphinyl)oxy]-N-phenylhexaneamide
  参考文献：
  名称：

  Phosphorus-Based SAHA Analogues as Histone Deacetylase Inhibitors

  摘要：

  graphicThree analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Anti proliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

  DOI：

  10.1021/ol035056n