3-(3,4,5-trimethoxyphenyl)acrylic acid 5-methoxy-4-[2-methyl-3-(3-methylbut-2-enyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester | 251111-15-6

• 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: 3-(3,4,5-trimethoxyphenyl)acrylic acid 5-methoxy-4-[2-methyl-3-(3-methylbut-2-enyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester
• 英文别名: CKD 731；CDK-731；O-(3,4,5-trimethoxycinnamoyl)fumagillol；O-(3,4,5-Trimethoxy-trans-cinnamoyl)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-(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 251111-15-6
• 化学式: C₂₈H₃₈O₈
• 分子量: 502.605
• InChiKey: YALIVVKJRYVKNB-GGHPKCFRSA-N

物化性质

• 沸点：
  602.6±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  8

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 、 (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3,4,5-trimethoxyphenyl)acrylic acid 5-methoxy-4-[2-methyl-3-(3-methylbut-2-enyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester
  参考文献：
  名称：

  Design and synthesis of highly potent fumagillin analogues from homology modeling for a human MetAP-2

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00577-6

文献信息

• Design, synthesis and evaluation of a series of novel fumagillin analogues
  作者：Maria Fardis、Hyung-Jung Pyun、James Tario、Haolun Jin、Choung U Kim、Judy Ruckman、Yun Lin、Louis Green、Brian Hicke

  DOI：10.1016/j.bmc.2003.08.031

  日期：2003.11

  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.
• 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.