5-{(3aS,5R,6R,6aS)-6-[(E)-(R)-7-(3-Azido-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester | 141887-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-{(3aS,5R,6R,6aS)-6-[(E)-(R)-7-(3-Azido-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester
• CAS: 141887-95-8
• 化学式: C₂₇H₃₇N₃O₄
• 分子量: 467.608
• InChiKey: VFBPICMQORNQMS-SISZJKGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  115.52
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-{(3aS,5R,6R,6aS)-6-[(E)-(R)-7-(3-Azido-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以96%的产率得到19-(3-azidophenyl)-15-epi-20-norisocarbacyclin
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4
• 作为产物：
  描述：

  13,14-dihydroxy-13,14-dihydroisocarbacyclin methyl ester 在 sodium tetrahydroborate 、 sodium periodate 、 cerium(III) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 8.05h， 生成 5-{(3aS,5R,6R,6aS)-6-[(E)-(R)-7-(3-Azido-phenyl)-3-hydroxy-hept-1-enyl]-5-hydroxy-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

  摘要：

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.

  DOI：

  10.1016/s0040-4020(01)88526-4