Fumarranol | 912569-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fumarranol
• 英文别名: (1S,5S,6S)-5-(hydroxymethyl)-1-methoxy-6-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]bicyclo[3.1.0]hexan-2-one
• CAS: 912569-37-0
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: CANZHCRPLGNWCR-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6-oxo-6-deoxyfumagillol	132746-88-4	C16H24O4	280.364
  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	fumagillol	108102-51-8	C16H26O4	282.38

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6S-(1'R,2'R-1',5'-dimethyl-1',2'-oxiranyl-4'-hexenyl)-5S-methoxymethyl-1S-methoxybicyclo[3.1.0]-2-hexanone	——	C17H26O4	294.391
  ——	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	——	C21H32O6	380.481
  ——	6S-(1'R,2'R-1',5'-dimethyl-1',2'-oxiranyl-4'-hexenyl)-5S-methoxy-4-oxobicyclo[3.1.0]hexane-1R-carbaldehyde	——	C16H22O4	278.348
  ——	6S-(1'R,2'R-1',5'-dimethyl-1',2'-oxiranyl-4'-hexenyl)-3-(furan-2-ylmethylene)-5S-hydroxymethyl-1S-methoxybicyclo[3.1.0]-2-hexanone	——	C21H26O5	358.434
  ——	2-(((1S,5S,6S)-5-methoxy-6-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-4-oxobicyclo[3.1.0]hexan-1-yl)methyl)isoindoline-1,3-dione	——	C24H27NO5	409.482

反应信息

• 作为反应物：
  描述：

  Fumarranol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95.2%的产率得到6S-(1'R,2'R-1',5'-dimethyl-1',2'-oxiranyl-4'-hexenyl)-5S-methoxy-4-oxobicyclo[3.1.0]hexane-1R-carbaldehyde
  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
• 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 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 Fumarranol
  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.