{3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-yl]-4-oxo-4H-quinolin-1-yl}-acetic acid | 322002-12-0

• 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: {3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-yl]-4-oxo-4H-quinolin-1-yl}-acetic acid
• 英文别名: 2-[3-[(3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-2,5,8,11-tetraoxo-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-6-yl]-4-oxoquinolin-1-yl]acetic acid
• CAS: 322002-12-0
• 化学式: C₃₅H₄₇N₅O₈
• 分子量: 665.787
• InChiKey: XGEXIFZCHVEMIS-KYQRTGHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  182
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  {3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-yl]-4-oxo-4H-quinolin-1-yl}-acetic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 Petroleum ether 为溶剂， 反应 0.25h， 以100%的产率得到{3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-yl]-4-oxo-4H-quinolin-1-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of Apicidin-Derived Quinolone Derivatives:  Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents

  摘要：

  Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.

  DOI：

  10.1021/jm0001976
• 作为产物：
  描述：

  {3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-ylmethyl]-indol-1-yl}-acetic acid methyl ester 在 lithium hydroxide 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 {3-[(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-5,8,11,14-tetraoxo-12-(6-oxo-octyl)-tetradecahydro-4a,7,10,13-tetraaza-benzocyclododecen-9-yl]-4-oxo-4H-quinolin-1-yl}-acetic acid
  参考文献：
  名称：

  Synthesis of Apicidin-Derived Quinolone Derivatives:  Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents

  摘要：

  Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.

  DOI：

  10.1021/jm0001976