2-(5-Hydroxy-pentyl)-malonic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-(5-Hydroxy-pentyl)-malonic acid
• 英文别名: 2-(5-Hydroxypentyl)propanedioic acid；2-(5-hydroxypentyl)propanedioic acid
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: MMEMTQSHLYODPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-Hydroxy-pentyl)-malonic acid 在 palladium on activated charcoal sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-[5-(Formyl-hydroxy-amino)-pentyl]-N,N''-di-quinolin-6-yl-malonamide
  参考文献：
  名称：

  Design, synthesis, and activity of HDAC inhibitors with a N-formyl hydroxylamine head group

  摘要：

  Histone deacetylases (HDAC) are promising targets for cancer chemotherapy. HDAC inhibitors are thought to act in part by disrupting normal cell cycle regulation, resulting in apoptosis and/or differentiation of transformed cells. Several HDAC inhibitors, which contain hydrophobic tails and the Zn2+ chelator hydroxyamic acid as a head group, are potent inhibitors of HDACs both in vitro and in vivo. In this study, a related class of compounds with a N-formyl hydroxylamino head group has been synthesized and their ability to inhibit HDACs have been assayed in biochemical and cellular assays. These compounds were found to have comparable activities to suberoylanilide hydroxyamic acid (SAHA) in HDAC enzymatic assays and histone hyperacetylation cellular assays. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.055

文献信息

• Design, synthesis, and activity of HDAC inhibitors with a N-formyl hydroxylamine head group
  作者：Tom Y.H. Wu、Christian Hassig、Yiqin Wu、Sheng Ding、Peter G. Schultz

  DOI：10.1016/j.bmcl.2003.10.055

  日期：2004.1

  Histone deacetylases (HDAC) are promising targets for cancer chemotherapy. HDAC inhibitors are thought to act in part by disrupting normal cell cycle regulation, resulting in apoptosis and/or differentiation of transformed cells. Several HDAC inhibitors, which contain hydrophobic tails and the Zn2+ chelator hydroxyamic acid as a head group, are potent inhibitors of HDACs both in vitro and in vivo. In this study, a related class of compounds with a N-formyl hydroxylamino head group has been synthesized and their ability to inhibit HDACs have been assayed in biochemical and cellular assays. These compounds were found to have comparable activities to suberoylanilide hydroxyamic acid (SAHA) in HDAC enzymatic assays and histone hyperacetylation cellular assays. (C) 2003 Elsevier Ltd. All rights reserved.