(3,4-Dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid ethyl ester | 212578-45-5

• 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: (3,4-Dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-(3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetate
• CAS: 212578-45-5
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: ZZABUGSBMMQHMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,4-Dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid ethyl ester 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-(3,4-dihydro-4-methyl-2H-1,4-benzoxazine-2-yl)acetic acid
  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：

  2-(苯基亚甲基氨基)苯酚 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 (3,4-Dihydro-2H-benzo[1,4]oxazin-2-yl)-acetic acid ethyl ester
  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

• NMR studies of new heterocycles tethered to purine moieties with anticancer activity
  作者：Nerea Fernández-Sáez、Joaquín M. Campos、María Encarnación Camacho、María Dora Carrión

  DOI：10.1002/mrc.4871

  日期：2019.6

  study reports the unambiguous assignment of each signal in the H and C NMR spectra in benzoxazine derivatives (3a–d), including elongation of the side chain, tetrahydroquinolines (5a–d), and pyridoxazine derivatives (11a–b) in which a pyridine ring is merged to the oxazine heterocycle, using one‐ and two‐dimensional resonance techniques. The assignment of derivatives 1, 2, 4, and 6–10, the precursors

  癌症是我们社会面临的最大威胁之一，因为它是导致死亡的主要原因之一。近年来已经开发了许多活性化合物来解决这个问题。一些具有有趣的抗增殖活性的嘌呤衍生物先前已通过将苯并稠合杂环与取代的嘌呤相结合而合成。为了提高活性并更深入地了解构效关系，获得了新的化合物。这些变化包括一些生物等排置换，如杂环氧原子的消除或六元杂环和取代嘌呤之间连接链的延长。通过这种方式，这些新型嘌呤衍生物家族的合成和生物学评价与六元杂环部分 3a-d、5a-d 和 11a-b 相连，已经描述了它们被设计和评估为抗癌剂。这些新化合物的结构已通过 H 和 C 核磁共振 (NMR) 和质谱法确定。为了通过使用二维技术证实它们的骨架，对其中的一些进行了更详细的研究，并对所有最终化合物进行了元素分析。本研究报告了苯并恶嗪衍生物 (3a-d) 的 H 和 C NMR 光谱中每个信号的明确分配，包括侧链的伸长、四氢喹啉 (5a-d) 和吡哆嗪衍生物
• Mayer, Stanislas; Guillaumet, Gerald; Merour, Jean-Yves, Heterocycles, 2001, vol. 55, # 10, p. 1873 - 1888
  作者：Mayer, Stanislas、Guillaumet, Gerald、Merour, Jean-Yves

  DOI：——

  日期：——
• 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.