19-(3-azidophenyl)-15-dehydro-20-norisocarbacyclin methyl ester | 140900-69-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 19-(3-azidophenyl)-15-dehydro-20-norisocarbacyclin methyl ester
• CAS: 140900-69-2
• 化学式: C₂₇H₃₅N₃O₄
• 分子量: 465.593
• InChiKey: YAPWJXPTWLMMBE-HIQMWJOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 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：
  0.56
• 拓扑面积：
  112.36
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  19-(3-azidophenyl)-15-dehydro-20-norisocarbacyclin methyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.22h， 生成 5-{(3aS,5R,6R,6aS)-6-[(S)-7-(3-Amino-phenyl)-3-hydroxy-heptyl]-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
• 作为产物：
  描述：

  13,14-dihydroxy-13,14-dihydroisocarbacyclin methyl ester 在 sodium periodate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.0h， 生成 19-(3-azidophenyl)-15-dehydro-20-norisocarbacyclin 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