(R)-4-Allyl-8-benzyloxy-octanoic acid | 1026647-32-4

• 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: (R)-4-Allyl-8-benzyloxy-octanoic acid
• 英文别名: (4R)-8-phenylmethoxy-4-prop-2-enyloctanoic acid
• CAS: 1026647-32-4
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: OMWDIBHSJKGSSL-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-Allyl-8-benzyloxy-octanoic acid 在 sodium hydroxide 、 potassium phosphate 、 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 palladium hydroxide - carbon 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 131.34h， 生成 (4S)-8-<<(4-chlorophenyl)sulfonyl>amino>-4-<3-(3-pyridinyl)propyl>octanoic acid
  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：

  Methanesulfonic acid (S)-2-allyl-6-benzyloxy-hexyl ester 在 氢氧化钾 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 39.5h， 生成 (R)-4-Allyl-8-benzyloxy-octanoic acid
  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