acetic acid 4-chloromethyl-3-(1,5-dimethylhexa-1,4-dienyl)-4-hydroxy-2-methoxycyclohexyl ester | 654055-68-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: acetic acid 4-chloromethyl-3-(1,5-dimethylhexa-1,4-dienyl)-4-hydroxy-2-methoxycyclohexyl ester
• CAS: 654055-68-2
• 化学式: C₁₈H₂₉ClO₄
• 分子量: 344.879
• InChiKey: USHLSTKCBXEQHX-KDKURVRZSA-N

物化性质

• 沸点：
  412.2±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  acetic acid 4-chloromethyl-3-(1,5-dimethylhexa-1,4-dienyl)-4-hydroxy-2-methoxycyclohexyl ester 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 [(3R,4S,5S,6R)-5-methoxy-4-[(2E)-6-methylhepta-2,5-dien-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Design, synthesis and evaluation of a series of novel fumagillin analogues

  摘要：

  A series of fumagillin analogues targeted at understanding tolerability of MetAP2 toward substitution at C4 and C6 were synthesized. Initially, the C6 side chain was maintained as cinnamoyl ester and C4 was modified. It was concluded that replacing the natural C4 of fumagillin with a benzyl oxime at C4 resulted in moderate loss of activity toward binding to MetAP2. Placement of a primary or secondary carbamate at C6 did not improve the potency of compounds toward inhibition of MetAP2. However, the inhibitory activity against MetAP2 was gained back by placing polar groups such as piperazinyl carbamate at C6. Small alkyl substituents on the amine of piperazinyl carbamate were well tolerated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.031
• 作为产物：
  描述：

  acetic acid 4-chloromethyl-4-hydroxy-2-methoxy-3-[2-methyl-3-(3-methylbut-2-enyl)oxiranyl]cyclohexyl ester 在 正丁基锂 、 六氯化钨 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以71.2%的产率得到acetic acid 4-chloromethyl-3-(1,5-dimethylhexa-1,4-dienyl)-4-hydroxy-2-methoxycyclohexyl ester
  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