Carbamic acid (3R,4S,5S,6R)-4-acetyl-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester | 669064-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Carbamic acid (3R,4S,5S,6R)-4-acetyl-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester
• CAS: 669064-71-5
• 化学式: C₁₁H₁₇NO₅
• 分子量: 243.26
• InChiKey: VFTQUOJEDDJBAH-LOKLDPHHSA-N

物化性质

• 沸点：
  423.3±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  91.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  O-苄基羟胺 、 Carbamic acid (3R,4S,5S,6R)-4-acetyl-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到[(3R,4S,5S,6R)-5-methoxy-4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]-1-oxaspiro[2.5]octan-6-yl] carbamate
  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：

  [(3R,4S,5S,6R)-5-methoxy-4-[(2E)-6-methylhepta-2,5-dien-2-yl]-1-oxaspiro[2.5]octan-6-yl] carbamate 在 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以74%的产率得到Carbamic acid (3R,4S,5S,6R)-4-acetyl-5-methoxy-1-oxa-spiro[2.5]oct-6-yl ester
  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