3-(4-fluorophenyl)-6-methyl-2H-1,4-benzoxazine | 338391-73-4

• 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-fluorophenyl)-6-methyl-2H-1,4-benzoxazine
• CAS: 338391-73-4
• 化学式: C₁₅H₁₂FNO
• 分子量: 241.265
• InChiKey: AUXBNOADBOUOEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  358.1±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氨基对甲苯酚 、 2-溴-4'-氟苯乙酮 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.75h， 生成 3-(4-fluorophenyl)-6-methyl-2H-1,4-benzoxazine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics

  摘要：

  A small library of 2H-benzo[b][1,4] oxazine derivative was synthesized and their biological activity was tested on HepG2 cells under normoxic and hypoxic conditions. From preliminary screening, we found compound 10 and 11 specifically inhibit hypoxic cancer cell growth IC50 87 +/- 1.8 mu M and IC50 10 +/- 3.7 mu M while sparing 'normoxic' cells IC50 > 600 M and > 1 mM (not applicable), respectively. We tested the effect of 10 on MTT, clonogenic and hypoxia induced genes. The MTT correlates with clonogenic assays and most importantly compound 10 down regulates hypoxia induces genes (HIF-1 alpha, P21 and VEGF) appropriately. We are in the process to explore the molecular mechanism of action of oxazine derivative compounds on hypoxia tumor cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.110

文献信息

• RETINOIC ACID RECEPTOR ANTAGONISTS AS CHAPERONE-MEDIATED AUTOPHAGY MODULATORS AND USES THEREOF
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY

  公开号：US20150166492A1

  公开（公告）日：2015-06-18

  Compounds, compositions and methods are provided for selectively activating chaperone-mediated autophagy (CMA), protecting cells from oxidative stress, proteotoxicity and lipotoxicity, and/or antagonizing activity of retinoic acid receptor alpha (RARα) in subjects in need thereof.

  本发明提供了一种选择性激活伴随蛋白介导的自噬（CMA），保护细胞免受氧化应激、蛋白毒性和脂毒性的化合物、组合物和方法，并/或在需要的受试者中拮抗视黄酸受体α（RARα）的活性。
• RETINOIC ACID RECEPTOR ANTAGONISTS AS CHAPERONE-MEDIATED AUTHOPHAGY MODULATORS AND USES THEREOF
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE, INC.

  公开号：US20170037039A1

  公开（公告）日：2017-02-09

  Compounds, compositions and methods are provided for selectively activating chaperone-mediated autophagy (CMA), protecting cells from oxidative stress, proteotoxicity and lipotoxicity, and/or antagonizing activity of retinoic acid receptor alpha (RARα) in subjects in need thereof.
• US9512092B2
  申请人：——

  公开号：US9512092B2

  公开（公告）日：2016-12-06
• Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics
  作者：Bhaskar C. Das、Ankanahlli V. Madhukumar、Jaime Anguiano、Sridhar Mani

  DOI：10.1016/j.bmcl.2009.05.110

  日期：2009.8

  A small library of 2H-benzo[b][1,4] oxazine derivative was synthesized and their biological activity was tested on HepG2 cells under normoxic and hypoxic conditions. From preliminary screening, we found compound 10 and 11 specifically inhibit hypoxic cancer cell growth IC50 87 +/- 1.8 mu M and IC50 10 +/- 3.7 mu M while sparing 'normoxic' cells IC50 > 600 M and > 1 mM (not applicable), respectively. We tested the effect of 10 on MTT, clonogenic and hypoxia induced genes. The MTT correlates with clonogenic assays and most importantly compound 10 down regulates hypoxia induces genes (HIF-1 alpha, P21 and VEGF) appropriately. We are in the process to explore the molecular mechanism of action of oxazine derivative compounds on hypoxia tumor cells. (C) 2009 Elsevier Ltd. All rights reserved.