8-(4-Fluoro-benzenesulfonylamino)-4-(3-pyridin-3-yl-propyl)-octanoic acid methyl ester | 1026677-68-8

• 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: 8-(4-Fluoro-benzenesulfonylamino)-4-(3-pyridin-3-yl-propyl)-octanoic acid methyl ester
• 英文别名: Methyl 8-[(4-fluorophenyl)sulfonylamino]-4-(3-pyridin-3-ylpropyl)octanoate
• CAS: 1026677-68-8
• 化学式: C₂₃H₃₁FN₂O₄S
• 分子量: 450.575
• InChiKey: CTGQDDHAYWBZHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(4-Fluoro-benzenesulfonylamino)-4-(3-pyridin-3-yl-propyl)-octanoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 8-(p-fluorophenylsulfonamido)-4-[3-(pyridin-3-yl)-propyl]-octanoic acid
  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：

  diethyl [3-(pyridin-3-yl)-propyl]-malonate 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium azide 、 18-冠醚-6 、 水 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 、 sodium iodide 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 169.58h， 生成 8-(4-Fluoro-benzenesulfonylamino)-4-(3-pyridin-3-yl-propyl)-octanoic acid methyl ester
  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