methyl (3S,6S,9S)-9-acetamido-6-[5-(hydroxycarbamoyl)pentyl]-5,8-dioxo-4,7-diazabicyclo[9.3.1]pentadeca-1(14),11(15),12-triene-3-carboxylate | 939435-75-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (3S,6S,9S)-9-acetamido-6-[5-(hydroxycarbamoyl)pentyl]-5,8-dioxo-4,7-diazabicyclo[9.3.1]pentadeca-1(14),11(15),12-triene-3-carboxylate
• 英文别名: methyl (3S,6S,9S)-9-acetamido-6-[6-(hydroxyamino)-6-oxohexyl]-5,8-dioxo-4,7-diazabicyclo[9.3.1]pentadeca-1(14),11(15),12-triene-3-carboxylate
• CAS: 939435-75-3
• 化学式: C₂₃H₃₂N₄O₇
• 分子量: 476.53
• InChiKey: MEJRAHCJERXHEQ-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 Pd-BaSO₄ 三乙基硅烷 、 4-二甲氨基吡啶 、 lithium hydroxide 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、68.95 kPa 条件下， 反应 36.0h， 生成 methyl (3S,6S,9S)-9-acetamido-6-[5-(hydroxycarbamoyl)pentyl]-5,8-dioxo-4,7-diazabicyclo[9.3.1]pentadeca-1(14),11(15),12-triene-3-carboxylate
  参考文献：
  名称：

  Design and Synthesis of a Potent Histone Deacetylase Inhibitor

  摘要：

  Histone deacetylase (HDAC) inhibitors have potential for cancer therapy. An HDAC inhibitor based on a cyclic peptide mimic of known structure, linked by an aliphatic chain to a hydroxamic acid, was designed and synthesized. The chimeric compound showed potent competitive inhibition of nuclear HDACs, with an IC50 value of 46 nM and a K-i value of 13.7 nM. The designed inhibitor showed 4-fold selectivity for HDAC1 (57 nM) over HDAC8 (231 nM).

  DOI：

  10.1021/jm061082q

文献信息

• Design and Synthesis of a Potent Histone Deacetylase Inhibitor
  作者：Tao Liu、Galina Kapustin、Felicia A. Etzkorn

  DOI：10.1021/jm061082q

  日期：2007.5.1

  Histone deacetylase (HDAC) inhibitors have potential for cancer therapy. An HDAC inhibitor based on a cyclic peptide mimic of known structure, linked by an aliphatic chain to a hydroxamic acid, was designed and synthesized. The chimeric compound showed potent competitive inhibition of nuclear HDACs, with an IC50 value of 46 nM and a K-i value of 13.7 nM. The designed inhibitor showed 4-fold selectivity for HDAC1 (57 nM) over HDAC8 (231 nM).