2-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}-4-methyl-3,4-dihydro-2H-1,4-benzoxazine | 212578-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}-4-methyl-3,4-dihydro-2H-1,4-benzoxazine
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-4-methyl-2,3-dihydro-1,4-benzoxazine-2-carboxamide
• CAS: 212578-41-1
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: MJNHULYJMJMWRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}-4-methyl-3,4-dihydro-2H-1,4-benzoxazine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以65%的产率得到2-(3,4-dimethoxyphenyl)-N-[(4-methyl-2,3-dihydro-1,4-benzoxazin-2-yl)methyl]ethanamine
  参考文献：
  名称：

  New Substituted 1,4-Benzoxazine Derivatives with Potential Intracellular Calcium Activity

  摘要：

  Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3,4-dihydro-2[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1,4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.

  DOI：

  10.1021/jm970795t
• 作为产物：
  描述：

  4-甲基-3,4-二氢-2H-1,4-苯并噁嗪-2-羧酸 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.08h， 生成 2-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}-4-methyl-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  New Substituted 1,4-Benzoxazine Derivatives with Potential Intracellular Calcium Activity

  摘要：

  Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3,4-dihydro-2[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1,4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.

  DOI：

  10.1021/jm970795t

文献信息

• New Substituted 1,4-Benzoxazine Derivatives with Potential Intracellular Calcium Activity
  作者：Anne-Sophie Bourlot、Isabel Sánchez、Georges Dureng、Gérald Guillaumet、Roy Massingham、André Monteil、Eileen Winslow、M. Dolors Pujol、Jean-Yves Mérour

  DOI：10.1021/jm970795t

  日期：1998.8.1

  Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3,4-dihydro-2[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1,4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.