2-(1-Adamantyl)-6-methyl-3,1-benzoxazin-4-one | 318499-27-3

• 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-(1-Adamantyl)-6-methyl-3,1-benzoxazin-4-one
• CAS: 318499-27-3
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: JTGVLPYMCGYWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-Adamantyl)-6-methyl-3,1-benzoxazin-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 N-[4-methyl-2-[[(5-methylfuran-2-yl)methylideneamino]carbamoyl]phenyl]adamantane-1-carboxamide
  参考文献：
  名称：

  Synthesis, Antitumor Activity, and Anti-HIV-1 Testing of Certain Heterocyclic Systems Containing an Adamantane Nucleus

  摘要：

  A new series of substituted 2-(1-adamantyl)-4H-3, 1-benzoxazin-4-ones and 2-(1-adamantyl)-3-amino or alkyl-3,4-dihydroquinazolin-4-ones have been synthesized and tested for their antitumor and antiviral activities, Among the tested compounds, compounds 5a and 5b exhibited a broad spectrum antitumor activity with full panel (MG-MID) median growth inhibition (GI(50)) values of 3.2 and 4.9 muM respectively. Meanwhile, compounds 5c, 5d, 5h, 5i, and 5j showed moderate selectivity towards leukemia cell lines. On the other hand, compounds 4a and 4b possessed moderate Anti-HIV-1 potency with EC50 values of 50.3 and 69.2 muM respectively. Detailed synthesis, spectroscopic, and biological data are reported.

  DOI：

  10.1002/1521-4184(200010)333:10<323::aid-ardp323>3.0.co;2-u
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-(1-Adamantyl)-6-methyl-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Synthesis, Antitumor Activity, and Anti-HIV-1 Testing of Certain Heterocyclic Systems Containing an Adamantane Nucleus

  摘要：

  A new series of substituted 2-(1-adamantyl)-4H-3, 1-benzoxazin-4-ones and 2-(1-adamantyl)-3-amino or alkyl-3,4-dihydroquinazolin-4-ones have been synthesized and tested for their antitumor and antiviral activities, Among the tested compounds, compounds 5a and 5b exhibited a broad spectrum antitumor activity with full panel (MG-MID) median growth inhibition (GI(50)) values of 3.2 and 4.9 muM respectively. Meanwhile, compounds 5c, 5d, 5h, 5i, and 5j showed moderate selectivity towards leukemia cell lines. On the other hand, compounds 4a and 4b possessed moderate Anti-HIV-1 potency with EC50 values of 50.3 and 69.2 muM respectively. Detailed synthesis, spectroscopic, and biological data are reported.

  DOI：

  10.1002/1521-4184(200010)333:10<323::aid-ardp323>3.0.co;2-u

文献信息

• Synthesis, Antitumor Activity, and Anti-HIV-1 Testing of Certain Heterocyclic Systems Containing an Adamantane Nucleus
  作者：Magda A. El-Sherbeny

  DOI：10.1002/1521-4184(200010)333:10<323::aid-ardp323>3.0.co;2-u

  日期：2000.10

  A new series of substituted 2-(1-adamantyl)-4H-3, 1-benzoxazin-4-ones and 2-(1-adamantyl)-3-amino or alkyl-3,4-dihydroquinazolin-4-ones have been synthesized and tested for their antitumor and antiviral activities, Among the tested compounds, compounds 5a and 5b exhibited a broad spectrum antitumor activity with full panel (MG-MID) median growth inhibition (GI(50)) values of 3.2 and 4.9 muM respectively. Meanwhile, compounds 5c, 5d, 5h, 5i, and 5j showed moderate selectivity towards leukemia cell lines. On the other hand, compounds 4a and 4b possessed moderate Anti-HIV-1 potency with EC50 values of 50.3 and 69.2 muM respectively. Detailed synthesis, spectroscopic, and biological data are reported.