ethyl 8-((2R,3R)-3-((1S,5S,6S)-5-(hydroxymethyl)-1-methoxy-2-oxobicyclo[3.1.0]hexan-6-yl)-3-methyloxiran-2-yl)oct-6-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 8-((2R,3R)-3-((1S,5S,6S)-5-(hydroxymethyl)-1-methoxy-2-oxobicyclo[3.1.0]hexan-6-yl)-3-methyloxiran-2-yl)oct-6-enoate
• 英文别名: ethyl (E)-8-[(2R,3R)-3-[(1S,5S,6S)-5-(hydroxymethyl)-1-methoxy-2-oxo-6-bicyclo[3.1.0]hexanyl]-3-methyloxiran-2-yl]oct-6-enoate
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: RFFMPONFDJMPBV-OKKFGMNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  6

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 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丙基高钌酸铵 氢氧化钾 、 3 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 8-((2R,3R)-3-((1S,5S,6S)-5-(hydroxymethyl)-1-methoxy-2-oxobicyclo[3.1.0]hexan-6-yl)-3-methyloxiran-2-yl)oct-6-enoate
  参考文献：
  名称：

  Fumarranol, a Rearranged Fumagillin Analogue That Inhibits Angiogenesis in Vivo

  摘要：

  The fumagillin family of natural products inhibits angiogenesis through the irreversible inhibition of the type 2 methionine aminopeptidase (MetAP2). Herein is reported a novel fumagillin analogue named fumarranol. It is shown that, like fumagillin, fumarranol selectively inhibits MetAP2 and endothelial cell proliferation. It is also active in a mouse model of angiogenesis in vivo. Unlike TNP-470, fumarranol does not covalently bind to MetAP2. Fumarranol may serve as a lead for a new class of angiogenesis inhibitors.

  DOI：

  10.1021/jm060559v

文献信息

• Fumarranol, a Rearranged Fumagillin Analogue That Inhibits Angiogenesis in Vivo
  作者：Jun Lu、Curtis R. Chong、Xiaoyi Hu、Jun O. Liu

  DOI：10.1021/jm060559v

  日期：2006.9.1

  The fumagillin family of natural products inhibits angiogenesis through the irreversible inhibition of the type 2 methionine aminopeptidase (MetAP2). Herein is reported a novel fumagillin analogue named fumarranol. It is shown that, like fumagillin, fumarranol selectively inhibits MetAP2 and endothelial cell proliferation. It is also active in a mouse model of angiogenesis in vivo. Unlike TNP-470, fumarranol does not covalently bind to MetAP2. Fumarranol may serve as a lead for a new class of angiogenesis inhibitors.