4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid | 212578-39-7

• 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: 4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid
• 英文别名: 4-benzyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid；4-benzyl-2,3-dihydro-1,4-benzoxazine-2-carboxylic acid
• CAS: 212578-39-7
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: DDFHPFXSVBIAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 24.08h， 生成 4-benzyl-2-{4-[(p-fluorophenyl)-1-piperazinyl]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
• 作为产物：
  描述：

  2-氨基苯酚 在 lithium hydroxide monohydrate 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 40.0h， 生成 4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid
  参考文献：
  名称：

  Discovery of Dihydro-1,4-Benzoxazine Carboxamides as Potent and Highly Selective Inhibitors of Sirtuin-1

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00017

文献信息

• Nouveaux dérivés de la pyrazolobenzoxazine, leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments et compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0197807A1

  公开（公告）日：1986-10-15

  L'invention concerne des nouveaux dérivés de la pyrazolobenzoxazine ainsi que leurs sels avec les acides de formule : où R est hydrogène, alkyle (C1-C5), cycloalkylalkyle (C4-C7), aralkyle éventuellement substitué, alkényle, alkynyle (C3-C5) et X est hydrogène ou CH2-S-Alk, Alk représentant un alkyle (C1-C5), leur procédé de préparation, leur application à titre de médicaments, les compositions les renfermant, et des intermédiaires.

  本发明涉及新的吡唑并噁嗪衍生物及其与酸（式中 R 为氢、(C1-C5)烷基、(C4-C7)环烷基、任选取代的芳基、烯基、(C3-C5)炔基）的盐，X 为氢或 CH2-S-Alk，Alk 代表(C1-C5)烷基，本发明还涉及它们的制备工艺、药物用途、含有它们的组合物和中间体。
• Discovery of Dihydro-1,4-Benzoxazine Carboxamides as Potent and Highly Selective Inhibitors of Sirtuin-1
  作者：Martin Spinck、Matthias Bischoff、Philipp Lampe、Franz-Josef Meyer-Almes、Sonja Sievers、Heinz Neumann

  DOI：10.1021/acs.jmedchem.1c00017

  日期：2021.5.13
• 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.