5-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)-methyl]-1,2,4-oxadiazole | 1235444-30-0

• 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-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)-methyl]-1,2,4-oxadiazole
• 英文别名: 4-[2-[3-[(6-Hydroxy-2,2,7,8-tetramethyl-3,4-dihydrochromen-5-yl)methyl]-1,2,4-oxadiazol-5-yl]ethyl]benzene-1,2-diol
• CAS: 1235444-30-0
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: VHKVUYFMYGACEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(3,4-dimethoxyphenethyl)-3-[(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-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， 反应 2.0h， 以58%的产率得到5-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)-methyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of a second generation chroman/catechol hybrids and evaluation of their activity in protecting neuronal cells from oxidative stress-induced cell death

  摘要：

  A new generation of chroman/catechol hybrids bearing heterocyclic five-membered rings, such as 1,2, 4-oxadiazole 1,3,4-oxadiazole, 1,2,3-triazole, tetrazole and isoxazole, were designed and synthesized. The activity of the new derivatives against oxidative stress induced neuronal damage, was evaluated using glutamate-challenged hippocampal HT22 cells.Compound 3 in which a 3,4-dimethoxyphenyl moiety, is directly attached to the 1,2,4-oxadiazole ring was the most active among the 2-substituted chroman analogues, with EC50 = 254 +/- 65 nM. Concerning the 5-subtituted chroman analogues, isoxazole derivative 29 exhibited the strongest activity (EC50 = 245 +/- 38 nM). However, 29 was cytotoxic at concentrations higher than 1 mu M, while the triazole analogue 24 (EC50 = 801 +/- 229 nM), was non-toxic at all concentrations tested. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.042

文献信息

• Synthesis of a second generation chroman/catechol hybrids and evaluation of their activity in protecting neuronal cells from oxidative stress-induced cell death
  作者：Maria Koufaki、Elissavet Theodorou、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2010.04.042

  日期：2010.6.1

  A new generation of chroman/catechol hybrids bearing heterocyclic five-membered rings, such as 1,2, 4-oxadiazole 1,3,4-oxadiazole, 1,2,3-triazole, tetrazole and isoxazole, were designed and synthesized. The activity of the new derivatives against oxidative stress induced neuronal damage, was evaluated using glutamate-challenged hippocampal HT22 cells.Compound 3 in which a 3,4-dimethoxyphenyl moiety, is directly attached to the 1,2,4-oxadiazole ring was the most active among the 2-substituted chroman analogues, with EC50 = 254 +/- 65 nM. Concerning the 5-subtituted chroman analogues, isoxazole derivative 29 exhibited the strongest activity (EC50 = 245 +/- 38 nM). However, 29 was cytotoxic at concentrations higher than 1 mu M, while the triazole analogue 24 (EC50 = 801 +/- 229 nM), was non-toxic at all concentrations tested. (C) 2010 Elsevier Ltd. All rights reserved.