5-(4-(1,2-dithiolan-3-yl)butyl)-1-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1H-tetrazole | 1190270-96-2

• 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)-1-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1H-tetrazole
• CAS: 1190270-96-2
• 化学式: C₂₃H₃₄N₄O₂S₂
• 分子量: 462.681
• InChiKey: NTZYNANTOZJMBL-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5-(4-(1,2-dithiolan-3-yl)butyl)-1-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1H-tetrazole 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到5-(4-(1,2-dithiolan-3-yl)butyl)-1-((3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1H-tetrazole
  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-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-(1,2-dithiolan-3-yl)pentanthioamide 在 叠氮基三甲基硅烷 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到5-(4-(1,2-dithiolan-3-yl)butyl)-1-((3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl)methyl)-1H-tetrazole
  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