ethyl 6-amino-2-<(3-pyridinyl)propyl>hexanoate | 144385-62-6

• 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: ethyl 6-amino-2-<(3-pyridinyl)propyl>hexanoate
• 英文别名: Ethyl 6-amino-2-(3-pyridin-3-ylpropyl)hexanoate
• CAS: 144385-62-6
• 化学式: C₁₆H₂₆N₂O₂
• 分子量: 278.395
• InChiKey: WTKYMQRDEILTMI-UHFFFAOYSA-N

物化性质

• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-2-<(3-pyridinyl)propyl>hexanoate 在 sodium hydroxide 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 三乙胺 、 cobalt(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 61.08h， 生成 8-[(4-氯苯基)磺酰氨基]-4-(3-吡啶-3-基丙基)辛酸
  参考文献：
  名称：

  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 4. 8-[[(4-Chlorophenyl)sulfonyl]amino]-4-[3-(3-pyridinyl)propyl]octanoic acid and analogs

  摘要：

  The title compound (10a) and its analogs were synthesized and found to possess two activities, the inhibition of the biosynthesis of thromboxane A2 and antagonism of its receptors. The in vitro and in vivo profile of these compounds as thromboxane receptor antagonists (TxRAs) and thromboxane synthase inhibitors (TxSIs) is described. 10a and its analogs displayed very potent TxRA activity in human washed platelets (IC50 almost-equal-to 10(-7)-10(-9) M) and dog saphenous vein (pA2 almost-equal-to 9) and also potent TxSI activity (IC50 almost-equal-to 10(-9) M). The good bioavailability and the long duration of action of some of these compounds was demonstrated using ex vivo measurement of the TxRA activity upon oral administration to guinea pigs. Compounds 10a, 20, and 33 potently inhibited arachidonic acid induced bronchoconstriction in guinea pigs.

  DOI：

  10.1021/jm00101a015
• 作为产物：
  描述：

  3-(3-溴丙基)吡啶氢溴酸盐 在 盐酸 、 氯化亚砜 、 sodium azide 、 18-冠醚-6 、 水 、 sodium 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 136.5h， 生成 ethyl 6-amino-2-<(3-pyridinyl)propyl>hexanoate
  参考文献：
  名称：

  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 4. 8-[[(4-Chlorophenyl)sulfonyl]amino]-4-[3-(3-pyridinyl)propyl]octanoic acid and analogs

  摘要：

  The title compound (10a) and its analogs were synthesized and found to possess two activities, the inhibition of the biosynthesis of thromboxane A2 and antagonism of its receptors. The in vitro and in vivo profile of these compounds as thromboxane receptor antagonists (TxRAs) and thromboxane synthase inhibitors (TxSIs) is described. 10a and its analogs displayed very potent TxRA activity in human washed platelets (IC50 almost-equal-to 10(-7)-10(-9) M) and dog saphenous vein (pA2 almost-equal-to 9) and also potent TxSI activity (IC50 almost-equal-to 10(-9) M). The good bioavailability and the long duration of action of some of these compounds was demonstrated using ex vivo measurement of the TxRA activity upon oral administration to guinea pigs. Compounds 10a, 20, and 33 potently inhibited arachidonic acid induced bronchoconstriction in guinea pigs.

  DOI：

  10.1021/jm00101a015