O-(3,4-dimethoxyphenylpropenoyl)-(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-ylacetamidoxime) | 1235444-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: O-(3,4-dimethoxyphenylpropenoyl)-(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-ylacetamidoxime)
• CAS: 1235444-21-9
• 化学式: C₂₇H₃₄N₂O₆
• 分子量: 482.577
• InChiKey: IYDDHPMLGFQNHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101.6
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O-(3,4-dimethoxyphenylpropenoyl)-(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-ylacetamidoxime) 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到5-[2-(3,4-dimethoxyphenyl)vinyl]-3-[(3,4-dihydro-6-methoxy-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
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 、 N'-hydroxy-2-(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-benzopyran-5-yl) acetamidine 在 三乙胺 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 0.5h， 以27%的产率得到O-(3,4-dimethoxyphenylpropenoyl)-(3,4-dihydro-6-methoxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-ylacetamidoxime)
  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