2-[3-[2-(3,5-Ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propyl]isoindole-1,3-dione | 1026514-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[3-[2-(3,5-Ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propyl]isoindole-1,3-dione
• CAS: 1026514-31-7
• 化学式: C₂₈H₃₄N₂O₄S
• 分子量: 494.655
• InChiKey: TXJQEJKAQUBODY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-[2-(3,5-Ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propyl]isoindole-1,3-dione 在 甲胺 作用下， 以 甲醇 为溶剂， 以91%的产率得到3-(3-Amino-propyl)-2-(3,5-di-tert-butyl-4-hydroxy-phenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 1. 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones

  摘要：

  A series of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones was synthesized in order to explore novel calcium antagonists with potent antiischemic activity. These compounds were designed to have, in addition to Ca2+ antagonistic activity, both Ca2+ overload prevention and antioxidant activity in one molecule. These three kinds of activity were evaluated by using a K+-depolarized rat aorta, a veratridine-induced Ca2+ overload model of rat cardiomyocytes, and a soybean lipoxygenase-induced lipid peroxidation model of rabbit low-density lipoprotein, respectively. In particular, 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one (7o) was found to be highly potent and possessed a well-balanced combination of these actions in vitro.

  DOI：

  10.1021/jm980335f
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲醛 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.5h， 生成 2-[3-[2-(3,5-Ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propyl]isoindole-1,3-dione
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 1. 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones

  摘要：

  A series of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(aminopropyl)thiazolidinones was synthesized in order to explore novel calcium antagonists with potent antiischemic activity. These compounds were designed to have, in addition to Ca2+ antagonistic activity, both Ca2+ overload prevention and antioxidant activity in one molecule. These three kinds of activity were evaluated by using a K+-depolarized rat aorta, a veratridine-induced Ca2+ overload model of rat cardiomyocytes, and a soybean lipoxygenase-induced lipid peroxidation model of rabbit low-density lipoprotein, respectively. In particular, 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one (7o) was found to be highly potent and possessed a well-balanced combination of these actions in vitro.

  DOI：

  10.1021/jm980335f