[(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 | 654055-63-7

• 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: [(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
• CAS: 654055-63-7
• 化学式: C₂₈H₃₈O₇
• 分子量: 486.606
• InChiKey: IGQQXQPKVKAEQJ-LMKOPFKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(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 在 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到
  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：

  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 、 正丁基锂 、 potassium tert-butylate 、 六氯化钨 、 potassium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.42h， 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

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.