Fumagalone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fumagalone
• 英文别名: (1R,2S,3S)-1-hydroxy-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxocyclohexane-1-carbaldehyde
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: UKNNCBXEELDDCU-SUJAAXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-甲氧基-4-[2-甲基-3-(3-甲基丁-2-烯基)环氧乙烷-2-基]-1-氧杂螺[2.5]辛烷-6-醇 在 四丙基高钌酸铵 、 sodium acetate 、 potassium carbonate 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 Fumagalone
  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

文献信息

• BIOMARKERS OF METAP2 INHIBITORS AND APPLICATIONS THEREOF
  申请人：SynDevRx, Inc.

  公开号：US20200129457A1

  公开（公告）日：2020-04-30

  The present disclosure relates to small molecule or polymer conjugated MetAP2 inhibitors. The present disclosure also relates to methods of treating, or ameliorating at least one symptom of metabolic dysfunction associated with a treatment in a subject having a disease, such as cancer. The present disclosure also relates to methods of treating, or ameliorating at least one symptom of cancer comprising administering a combination of a polymer conjugated MetAP2 inhibitors and at least one second agent wherein the second agent may induce metabolic dysfunction.
• Fumagalone, a Reversible Inhibitor of Type 2 Methionine Aminopeptidase and Angiogenesis
  作者：Guochun Zhou、Chiawei W. Tsai、Jun O. Liu

  DOI：10.1021/jm0341103

  日期：2003.7.1

  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.