(4R)-methyl 8-hydroxy-4-<3-(3-pyridinyl)propyl>octanoate | 145746-81-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R)-methyl 8-hydroxy-4-<3-(3-pyridinyl)propyl>octanoate
• 英文别名: methyl (4S)-8-hydroxy-4-(3-pyridin-3-ylpropyl)octanoate
• CAS: 145746-81-2
• 化学式: C₁₇H₂₇NO₃
• 分子量: 293.406
• InChiKey: ICRSEOZQDGRADQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-methyl 8-hydroxy-4-<3-(3-pyridinyl)propyl>octanoate 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 21.17h， 生成 (4R)-methyl 8-<<(4-chlorophenyl)sulfonyl>amino>-4-<3-(3-pyridinyl)propyl>octanoate
  参考文献：
  名称：

  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 5. Synthesis and evaluation of enantiomers of 8-[[(4-chlorophenyl)sulfonyl]amino]-4-(3-pyridinylalkyl)octanoic acid

  摘要：

  The enantiomers of 8-[[(4-chlorophenyl)sulfonyl]amino]-4-(3-pyridinylpropyl)octanoic acid (1) and its pyridinyl ether analog (2) were synthesized using the highly diastereoselective method of alkylation of acyloxazolidinone. These enantiomerically pure compounds were compared with the corresponding racemic compounds 1 and 2 for their in vitro activity. Compounds 1, 1R, and 1S and 2,2S, and 2R were equipotent as thromboxane receptor antagonists (TxRAs) and thromboxane synthase inhibitors (TxSIs) (IC50 = 2-30 nM). Upon oral administration to guinea pigs, the enantiomers inhibited the ex vivo U 46619-induced platelet aggregation with potency similar to that of the corresponding racemic compound. This indicates that the enantiomers have pharmacologic profile and bioavailability similar to that of the corresponding racemic compound.

  DOI：

  10.1021/jm00054a003
• 作为产物：
  描述：

  3-溴吡啶 在 potassium phosphate 、 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 palladium hydroxide - carbon 作用下， 以 环己烷 为溶剂， 反应 90.0h， 生成 (4R)-methyl 8-hydroxy-4-<3-(3-pyridinyl)propyl>octanoate
  参考文献：
  名称：

  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 5. Synthesis and evaluation of enantiomers of 8-[[(4-chlorophenyl)sulfonyl]amino]-4-(3-pyridinylalkyl)octanoic acid

  摘要：

  The enantiomers of 8-[[(4-chlorophenyl)sulfonyl]amino]-4-(3-pyridinylpropyl)octanoic acid (1) and its pyridinyl ether analog (2) were synthesized using the highly diastereoselective method of alkylation of acyloxazolidinone. These enantiomerically pure compounds were compared with the corresponding racemic compounds 1 and 2 for their in vitro activity. Compounds 1, 1R, and 1S and 2,2S, and 2R were equipotent as thromboxane receptor antagonists (TxRAs) and thromboxane synthase inhibitors (TxSIs) (IC50 = 2-30 nM). Upon oral administration to guinea pigs, the enantiomers inhibited the ex vivo U 46619-induced platelet aggregation with potency similar to that of the corresponding racemic compound. This indicates that the enantiomers have pharmacologic profile and bioavailability similar to that of the corresponding racemic compound.

  DOI：

  10.1021/jm00054a003