4-(7-Oxooxepan-4-yl)butyl methanesulfonate | 144385-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-(7-Oxooxepan-4-yl)butyl methanesulfonate
• CAS: 144385-71-7
• 化学式: C₁₁H₂₀O₅S
• 分子量: 264.343
• InChiKey: BPAJHEVCMWMJES-UHFFFAOYSA-N

物化性质

• 沸点：
  461.9±18.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(7-Oxooxepan-4-yl)butyl methanesulfonate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 氯化亚砜 、 sodium azide 、 草酰氯 、 potassium tert-butylate 、 水 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -60.0~25.0 ℃ 、101.33 kPa 条件下， 反应 129.75h， 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：

  甲基磺酰氯 、 4-(4-hydroxybutyl)-ε-caprolactone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到4-(7-Oxooxepan-4-yl)butyl methanesulfonate
  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

文献信息

• Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 4. 8-[[(4-Chlorophenyl)sulfonyl]amino]-4-[3-(3-pyridinyl)propyl]octanoic acid and analogs
  作者：Shripad S. Bhagwat、Candido Gude、Clay Boswell、Nicolina Contardo、David S. Cohen、Ronald Dotson、Janice Mathis、Warren Lee、Patricia Furness、Harry Zoganas

  DOI：10.1021/jm00101a015

  日期：1992.11

  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.