p-methoxycinnamic acid (3R,4S,5S,6R)-5-methoxy-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhex-4-enyl]-1-oxaspiro[2.5]oct-6-yl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: p-methoxycinnamic acid (3R,4S,5S,6R)-5-methoxy-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhex-4-enyl]-1-oxaspiro[2.5]oct-6-yl ester
• 英文别名: o-(4-methoxycinnamoyl)fumagillol；[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] (E)-3-(4-methoxyphenyl)prop-2-enoate
• 化学式: C₂₆H₃₄O₆
• 分子量: 442.552
• InChiKey: LGWFQYZLMHYDSC-CRBJPABCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基肉桂酸 、 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 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以88%的产率得到p-methoxycinnamic acid (3R,4S,5S,6R)-5-methoxy-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhex-4-enyl]-1-oxaspiro[2.5]oct-6-yl ester
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+

文献信息

• Design and synthesis of highly potent fumagillin analogues from homology modeling for a human MetAP-2
  作者：Cheol Kyu Han、Soon Kil Ahn、Nam Song Choi、Ryung Kee Hong、Seung Kee Moon、Hyoung Sik Chun、Sang Joon Lee、Jung Woo Kim、Chung Il Hong、Deukjoon Kim、Jeong Hyeok Yoon、Kyoung Tai No

  DOI：10.1016/s0960-894x(99)00577-6

  日期：2000.1

  New fumagillin analogues were designed through structure-based molecular modeling with a human methionine aminopeptidase-2. Among the fumagillin analogues, cinnamic acid eater derivative CKD-731 showed 1000-fold more potent proliferation inhibitory activity on endothelial cell than TNP-470. (C) 1999 Elsevier Science Ltd. All rights reserved.
• MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues
  作者：Vincent Rodeschini、Jean-Guy Boiteau、Pierre Van de Weghe、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo035065+

  日期：2004.1.1

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.