methyl-7-[(3-pyridyl)carbonyl]heptanoate | 362670-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-7-[(3-pyridyl)carbonyl]heptanoate
• CAS: 362670-92-6
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: ZIFHUWAHCACKIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.26
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl-7-[(3-pyridyl)carbonyl]heptanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 7-nicotinoylheptanoic acid
  参考文献：
  名称：

  Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors

  摘要：

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.

  DOI：

  10.1021/jm020154k
• 作为产物：
  描述：

  3-溴吡啶 、 甲基8-氯-8-氧代辛酸 在 正丁基锂 、 三甲基氯化锡 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 、 苯 为溶剂， 反应 1.5h， 以59%的产率得到methyl-7-[(3-pyridyl)carbonyl]heptanoate
  参考文献：
  名称：

  Structurally Simple Trichostatin A-Like Straight Chain Hydroxamates as Potent Histone Deacetylase Inhibitors

  摘要：

  A series of new, structurally simple trichostatin A (TSA)-like straight chain hydroxamates were prepared and evaluated for their ability to inhibit partially purified human histone deacetylase 1 (HDAC-1). Some of these compounds such as 8m, 8n, 12, and 15b exhibited potent HDAC inhibitory activity with low nanomolar IC50 values, comparable to natural TSA. These compounds induce hyperacetylation of histones in T24 human cancer cells and significantly inhibit proliferation in. various human cancer cells. They also induce expression of p21 and cause cell cycle blocks in human cancer cells. in this paper, we describe the synthesis of these new compounds as well as structure-activity relationship results from enzyme inhibition and alterations in cellular function.

  DOI：

  10.1021/jm020154k