5-(4-(1,2-dithiolan-3-yl)butyl)-3-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1,2,4-oxadiazole | 1190270-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(4-(1,2-dithiolan-3-yl)butyl)-3-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1,2,4-oxadiazole
• CAS: 1190270-37-1
• 化学式: C₂₄H₃₄N₂O₃S₂
• 分子量: 462.678
• InChiKey: MMKFUTUZVPZPIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(4-(1,2-dithiolan-3-yl)butyl)-3-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1,2,4-oxadiazole 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到5-(4-(1,2-dithiolan-3-yl)butyl)-3-((3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids

  摘要：

  Novel 1,2-dithiolane/chroman hybrids bearing heterocyclic rings such as 1,2,4- and 1,3,4-oxadiazole, 1,2,3-triazole and tetrazole were designed and synthesized. The neuroprotective activity of the new analogues was tested against oxidative stress-induced cell death of glutamate-challenged HT22 hippocampal neurons. Our results show that bioisosteric replacement of amide group in 2-position of the chroman moiety, by 1,3,4- oxadiazole did not affect activity. However, analogue 5 bearing the 1,2,4- oxadiazole moiety showed improved neuroprotective activity. The presence of nitrogen heterocycles strongly influences the neuroprotective activity of 5-substituted chroman derivatives, depending on the nature of heterocycle. Replacement of the amide group of the first generation analogues by 1,2,4- oxadiazole or 1,2,3-triazole resulted in significant improvement of the activity against glutamate induced oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.010
• 作为产物：
  描述：

  N'-(5-(1,2-dithiolan-3-yl)pentanoyloxy)-2-(6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl) acetamidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到5-(4-(1,2-dithiolan-3-yl)butyl)-3-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids

  摘要：

  Novel 1,2-dithiolane/chroman hybrids bearing heterocyclic rings such as 1,2,4- and 1,3,4-oxadiazole, 1,2,3-triazole and tetrazole were designed and synthesized. The neuroprotective activity of the new analogues was tested against oxidative stress-induced cell death of glutamate-challenged HT22 hippocampal neurons. Our results show that bioisosteric replacement of amide group in 2-position of the chroman moiety, by 1,3,4- oxadiazole did not affect activity. However, analogue 5 bearing the 1,2,4- oxadiazole moiety showed improved neuroprotective activity. The presence of nitrogen heterocycles strongly influences the neuroprotective activity of 5-substituted chroman derivatives, depending on the nature of heterocycle. Replacement of the amide group of the first generation analogues by 1,2,4- oxadiazole or 1,2,3-triazole resulted in significant improvement of the activity against glutamate induced oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.010