(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-oxo-octyl)-9-(1-propyl-1H-indol-3-ylmethyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone | 321798-73-6

• 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: (6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-oxo-octyl)-9-(1-propyl-1H-indol-3-ylmethyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone
• 英文别名: cyclo[Aoda-Trp(Pr)(Pr)-Ile-D-Pip]；(3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-9-(6-oxooctyl)-6-[(1-propylindol-3-yl)methyl]-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone
• CAS: 321798-73-6
• 化学式: C₃₆H₅₃N₅O₅
• 分子量: 635.847
• InChiKey: FXEYCWDKBFMJHM-MSIFXXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-oxo-octyl)-9-(1-propyl-1H-indol-3-ylmethyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone 在 臭氧 、 二甲基硫 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.17h， 以79%的产率得到(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-oxo-octyl)-9-(4-oxo-1-propyl-1,4-dihydro-quinolin-3-yl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone
  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：

  1-碘代丙烷 、 Apicidin A 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-oxo-octyl)-9-(1-propyl-1H-indol-3-ylmethyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone
  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

文献信息

• Synthesis of Apicidin-Derived Quinolone Derivatives:  Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents
  作者：Peter T. Meinke、Steven L. Colletti、George Doss、Robert W. Myers、Anne M. Gurnett、Paula M. Dulski、Sandra J. Darkin-Rattray、John J. Allocco、Stefan Galuska、Dennis M. Schmatz、Matthew J. Wyvratt、Michael H. Fisher

  DOI：10.1021/jm0001976

  日期：2000.12.1

  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.