(1R,2S,3S,4R)-1-(benzenesulfinylmethyl)-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexane-1,4-diol | 592517-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1R,2S,3S,4R)-1-(benzenesulfinylmethyl)-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexane-1,4-diol
• CAS: 592517-32-3
• 化学式: C₂₂H₃₂O₅S
• 分子量: 408.559
• InChiKey: ZUCOBGAJDKNFJH-KZDGWXISSA-N

物化性质

• 沸点：
  580.0±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4R)-1-(benzenesulfinylmethyl)-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexane-1,4-diol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59.1%的产率得到(2S,3S,4R)-4-(benzenesulfinylmethyl)-4-hydroxy-2-methoxy-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexan-1-one
  参考文献：
  名称：

  Fumagalone, a Reversible Inhibitor of Type 2 Methionine Aminopeptidase and Angiogenesis

  摘要：

  Fumagillin and ovalicin constitute a family of structurally related natural products that possess antiangiogenic activity. We report the synthesis of a new fumagillin analogue, fumagalone, in which the spiroepoxide group is replaced with an aldehyde. Fumagalone inhibits type 2 methionine aminopeptidase (MetAP2) with IC50 = 8 muM and endothelial cell proliferation with IC50 = 52 nM. With dialysis and competition assays, it was unambiguously demonstrated that binding of fumagalone to MetAP2 is reversible.

  DOI：

  10.1021/jm0341103
• 作为产物：
  描述：

  (1R,2S,3S,4R)-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-(phenylsulfanylmethyl)cyclohexane-1,4-diol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (1R,2S,3S,4R)-1-(benzenesulfinylmethyl)-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]cyclohexane-1,4-diol
  参考文献：
  名称：

  Fumagalone, a Reversible Inhibitor of Type 2 Methionine Aminopeptidase and Angiogenesis

  摘要：

  Fumagillin and ovalicin constitute a family of structurally related natural products that possess antiangiogenic activity. We report the synthesis of a new fumagillin analogue, fumagalone, in which the spiroepoxide group is replaced with an aldehyde. Fumagalone inhibits type 2 methionine aminopeptidase (MetAP2) with IC50 = 8 muM and endothelial cell proliferation with IC50 = 52 nM. With dialysis and competition assays, it was unambiguously demonstrated that binding of fumagalone to MetAP2 is reversible.

  DOI：

  10.1021/jm0341103