(4S)-methyl 8-(benzyloxy)-4-(2-hydroxyethyl)octanoate | 143761-36-8

• 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: (4S)-methyl 8-(benzyloxy)-4-(2-hydroxyethyl)octanoate
• 英文别名: methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)-octanoate；methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate；methyl (4S)-4-(2-hydroxyethyl)-8-phenylmethoxyoctanoate
• CAS: 143761-36-8
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: BHOUYSWLALUZDK-INIZCTEOSA-N

物化性质

• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-methyl 8-(benzyloxy)-4-(2-hydroxyethyl)octanoate 在 偶氮二甲酸二异丙酯 、 palladium hydroxide - carbon 、 三苯基膦 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 2.0h， 生成 methyl (S)-8-hydroxy-4-[2-(pyridin-3-yloxy)ethyl]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：

  6-苄氧基己酸 在 氢氧化钾 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 锂硼氢 、 正丁基锂 、 水 、 sodium hydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.92h， 生成 (4S)-methyl 8-(benzyloxy)-4-(2-hydroxyethyl)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

文献信息

• Certain (arylsulfonamido- and imidazolyl-)-substituted carboxylic acids
  申请人：Ciba-Geigy Corporation

  公开号：US05153214A1

  公开（公告）日：1992-10-06

  The present invention is concerned with compounds of formula I ##STR1## wherein A, B, M, R, Ar and Het are as defined in the specification, pharmaceutically acceptable ester and amide derivatives thereof; N-oxides thereof, tetrazole derivatives thereof, and salts thereof. These compounds have valuable pharmacological activities, especially as inhibitors of thromboxane synthetase and as receptor antagonists of thromboxane A.sub.2 and prostaglandin H.sub.2.

  本发明涉及以下式I的化合物 ##STR1## 其中A、B、M、R、Ar和Het如规范中所定义，其药学上可接受的酯和酰胺衍生物；其N-氧化物，四唑衍生物和盐。这些化合物具有有价值的药理活性，特别是作为血栓素合酶的抑制剂和血栓素A.sub.2和前列腺素H.sub.2的受体拮抗剂。
• 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
  作者：Shripad S. Bhagwat、Candido Gude、David S. Cohen、Ron Dotson、Janice Mathis、Warren Lee、Patricia Furness

  DOI：10.1021/jm00054a003

  日期：1993.1

  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.