[(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] acetate | 669064-72-6

• 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: [(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] acetate
• CAS: 669064-72-6
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: NCRYCUMCKGOYJF-VRGQFVKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] acetate 在 甲醇 、 potassium carbonate 作用下， 以100%的产率得到Ethanone,1-[(3R,4S,5S,6R)-6-hydroxy-5-methoxy-1-oxaspiro[2.5]oct-4-yl]-,O-(phenylmethyl)oxime, (1E)-
  参考文献：
  名称：

  Investigation of novel fumagillin analogues as angiogenesis inhibitors

  摘要：

  Modification of fumagillin was conducted to develop MetAP-2 inhibitors with desirable pharmacological properties. Replacement of the C4 side chain by benzyloxime preserves the inhibitory activity against MetAP-2 enzyme. Fumagillin analogues containing the C4 benzyloxime moiety were found to be very sensitive to the nature of the C6 substituent on the inhibition activity of HUVEC proliferation. This lack of correlation between MetAP-2 and HUVEC activities might be due to the cellular metabolism of the compounds by epoxide hydrolase, which is present in the cell. Compound (E)-3d, containing ethylpiperazinyl carbamate at C6 position, exhibited antiangiogenic effects similar to TNP-470 on matrigel plug assay and rat corneal micropocket assay. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.008
• 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 、 4 A molecular sieve 、 六氯化钨 、 对甲苯磺酸 、 臭氧 、 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] acetate
  参考文献：
  名称：

  Investigation of novel fumagillin analogues as angiogenesis inhibitors

  摘要：

  Modification of fumagillin was conducted to develop MetAP-2 inhibitors with desirable pharmacological properties. Replacement of the C4 side chain by benzyloxime preserves the inhibitory activity against MetAP-2 enzyme. Fumagillin analogues containing the C4 benzyloxime moiety were found to be very sensitive to the nature of the C6 substituent on the inhibition activity of HUVEC proliferation. This lack of correlation between MetAP-2 and HUVEC activities might be due to the cellular metabolism of the compounds by epoxide hydrolase, which is present in the cell. Compound (E)-3d, containing ethylpiperazinyl carbamate at C6 position, exhibited antiangiogenic effects similar to TNP-470 on matrigel plug assay and rat corneal micropocket assay. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.008

文献信息

• Investigation of novel fumagillin analogues as angiogenesis inhibitors
  作者：Hyung-Jung Pyun、Maria Fardis、James Tario、Cheng Y. Yang、Judy Ruckman、Dwight Henninger、Haolun Jin、Choung U. Kim

  DOI：10.1016/j.bmcl.2003.10.008

  日期：2004.1

  Modification of fumagillin was conducted to develop MetAP-2 inhibitors with desirable pharmacological properties. Replacement of the C4 side chain by benzyloxime preserves the inhibitory activity against MetAP-2 enzyme. Fumagillin analogues containing the C4 benzyloxime moiety were found to be very sensitive to the nature of the C6 substituent on the inhibition activity of HUVEC proliferation. This lack of correlation between MetAP-2 and HUVEC activities might be due to the cellular metabolism of the compounds by epoxide hydrolase, which is present in the cell. Compound (E)-3d, containing ethylpiperazinyl carbamate at C6 position, exhibited antiangiogenic effects similar to TNP-470 on matrigel plug assay and rat corneal micropocket assay. (C) 2003 Elsevier Ltd. All rights reserved.