(3aR,5S,11bR)-5-(2-thienyl)-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione | 1146221-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3aR,5S,11bR)-5-(2-thienyl)-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione
• 英文别名: Pyranonaphthoquinone (PNQ) lactone, 11b；(11R,15R,17S)-17-thiophen-2-yl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3,5,7-tetraene-2,9,13-trione
• CAS: 1146221-17-1
• 化学式: C₁₉H₁₂O₅S
• 分子量: 352.367
• InChiKey: DIJUJQGZFMHBOT-RIPJAXHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (11R,15R,17S)-2,9-dimethoxy-17-thiophen-2-yl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,9-pentaen-13-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 (3aR,5S,11bR)-5-(2-thienyl)-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione
  参考文献：
  名称：

  Pyranonaphthoquinone Lactones: A New Class of AKT Selective Kinase Inhibitors Alkylate a Regulatory Loop Cysteine

  摘要：

  The naturally occurring pyranonaphthoquinone (PNQ) antibiotic lactoquinomycin and related aglycones were found to be selective inhibitors of the serine-threonine kinase AKT. A set of synthetic PNQs were prepared and a minimum active feature set and preliminary SAR were determined, PNQ lactones inhibit the proliferation of human tumor cell lines containing constitutively activated AKT and show expected effects on cellular biomarkers. Biochemical data are presented supporting a proposed bioreductive alkylation mechanism of action.

  DOI：

  10.1021/jm900075g