{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 | 321798-81-6

• 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: {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
• 英文别名: methyl 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]methyl]indol-1-yl]acetate
• CAS: 321798-81-6
• 化学式: C₃₆H₅₁N₅O₇
• 分子量: 665.83
• InChiKey: KLTFPCINVGRYAV-YZQQIFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  7

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-ylmethyl]-indol-1-yl}-acetic acid methyl ester 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， 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 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：

  溴乙酸甲酯 、 Apicidin A 在 四丁基碘化铵 、 sodium hydride 作用下， 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-ylmethyl]-indol-1-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Probing the elusive catalytic activity of vertebrate class IIa histone deacetylases

  摘要：

  It has been widely debated whether class IIa HDACs have catalytic deacetylase activity, and whether this plays any part in controlling gene expression. Herein, it has been demonstrated that class IIa HDACs isolated from mammalian cells are contaminated with other deacetylases, but can be prepared cleanly in Escherichia coli. These bacteria preparations have weak but measurable deacetylase activity. The low efficiency can be restored either by: mutation of an active site histidine to tyrosine, or by the use of a non-acetylated lysine substrate, allowing the development of assays to identify class IIa HDAC inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.025