carbonic acid 4-(1-benzyloxyiminoethyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester 4-nitrophenyl ester | 654055-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: carbonic acid 4-(1-benzyloxyiminoethyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester 4-nitrophenyl ester
• CAS: 654055-75-1
• 化学式: C₂₄H₂₆N₂O₈
• 分子量: 470.479
• InChiKey: QCWJIGHMMRQVOO-YFCZCXGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122.02
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-乙基哌嗪 、 carbonic acid 4-(1-benzyloxyiminoethyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester 4-nitrophenyl ester 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] 4-ethylpiperazine-1-carboxylate
  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：

  二(对硝基苯)碳酸酯 、 Ethanone,1-[(3R,4S,5S,6R)-6-hydroxy-5-methoxy-1-oxaspiro[2.5]oct-4-yl]-,O-(phenylmethyl)oxime, (1E)- 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以87%的产率得到carbonic acid 4-(1-benzyloxyiminoethyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester 4-nitrophenyl ester
  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