4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamide | 212578-42-2

• 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-carboxamide
• 英文别名: 4-Benzyl-2,3-dihydro-1,4-benzoxazine-2-carboxamide
• CAS: 212578-42-2
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: GALOEUXPVXRQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamide 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 生成 4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonitrile
  参考文献：
  名称：

  2-（2-咪唑啉基）取代的2,3-二氢-4 H -1,4-苯并噻嗪和3,4-二氢-2 H -1,4-苯并恶嗪的合成

  摘要：

  已经进行了2-（2-咪唑啉基）-1，4-苯并二恶烷的苯并恶嗪，苯并噻吨和苯并噻嗪衍生物的合成的研究。

  DOI：

  10.1002/jhet.5570220143
• 作为产物：
  描述：

  ethyl 4-benzyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 在 氨 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 4-benzyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamide
  参考文献：
  名称：

  2-（2-咪唑啉基）取代的2,3-二氢-4 H -1,4-苯并噻嗪和3,4-二氢-2 H -1,4-苯并恶嗪的合成

  摘要：

  已经进行了2-（2-咪唑啉基）-1，4-苯并二恶烷的苯并恶嗪，苯并噻吨和苯并噻嗪衍生物的合成的研究。

  DOI：

  10.1002/jhet.5570220143

文献信息

• [EN] SUBSTITUTED 4-BENZYL-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE-2CARBOXAMIDE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF MUSCARINIC ACETYCHOLINE RECEPTOR M1<br/>[FR] ANALOGUES SUBSTITUÉS DU 4-BENZYL-3,4-DIHYDRO-2H-BENZO[B] [1,4] OXAZINE-2-CARBOXAMIDE, UTILISÉS COMME MODULATEURS ALLOSTÉRIQUES POSITIFS DU RÉCEPTEUR MUSCARINIQUE DE L'ACÉTYLCHOLINE M1
  申请人：UNIV VANDERBILT

  公开号：WO2015080904A1

  公开（公告）日：2015-06-04

  In one aspect, the invention relates to N-substituted 3,4-dihydro-benzo[£][l,4]oxazine-2-carboxamide analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the muscarinic acetylcholine receptor M1 (mAChR M1); synthesis methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，这项发明涉及N-取代的3,4-二氢苯并[£][1,4]噁嗪-2-羧酰胺类似物，其衍生物和相关化合物，这些化合物可用作肌胆碱受体M1（mAChR M1）的正向变构调节剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与肌胆碱受体功能障碍相关的神经和精神疾病的方法。本摘要旨在作为在特定领域搜索的扫描工具，并不意味着对本发明的限制。
• 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.
• BUTLER, R. C. M.;CHAPLEO, CH. B.;MYERS, P. L.;WELBOURN, A. P., J. HETEROCYCL. CHEM., 1985, 22, N 1, 177-181
  作者：BUTLER, R. C. M.、CHAPLEO, CH. B.、MYERS, P. L.、WELBOURN, A. P.

  DOI：——

  日期：——
• SUBSTITUTED 4-BENZYL-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE-2CARBOXAMIDE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF MUSCARINIC ACETYCHOLINE RECEPTOR M1
  申请人：Vanderbilt University

  公开号：US20170022173A1

  公开（公告）日：2017-01-26

  In one aspect, the invention relates to N-substituted 3,4-dihydro-benzo[£][1,4]oxazine-2-carboxamide analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the muscarinic acetylcholine receptor M 1 (mAChR M 1 ); synthesis methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.