3-(4-chlorophenyl)-6-nitro-2H-benzo[b][1,4]oxazine | 112182-40-8

• 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-chlorophenyl)-6-nitro-2H-benzo[b][1,4]oxazine
• 英文别名: 3-(4-chlorophenyl)-6-nitro-2H-1,4-benzoxazine
• CAS: 112182-40-8
• 化学式: C₁₄H₉ClN₂O₃
• 分子量: 288.69
• InChiKey: CCLYABIRPCSNKR-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.2±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-6-nitro-2H-benzo[b][1,4]oxazine 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到6-Amino-3-(4-chlorophenyl)-2H-benzo[b][1,4]oxazine
  参考文献：
  名称：

  Shridhar, D. R.; Rao, K. Srinivasa; Rastogi, K., Journal of the Indian Chemical Society, 1986, vol. 63, p. 761 - 763

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 、 2-氨基-4-硝基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以52%的产率得到3-(4-chlorophenyl)-6-nitro-2H-benzo[b][1,4]oxazine
  参考文献：
  名称：

  A Convenient One-Step Synthesis of 3-Aryl-2H-1,4-benzoxazines

  摘要：

  DOI：

  10.1055/s-1981-29648

文献信息

• 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.
• SHRIDHAR, D. R.;SASTRY, C. V. R.;BANSAL, O. P.;RAO, P. P., SYNTHESIS, BRD, 1981, N 11, 912-913
  作者：SHRIDHAR, D. R.、SASTRY, C. V. R.、BANSAL, O. P.、RAO, P. P.

  DOI：——

  日期：——
• SHRIDHAR D. R.; RAO K. S.; RASTOGI K.; GANDHI S. S., J. INDIAN CHEM. SOC., 63,(1986) N 8, 761-763
  作者：SHRIDHAR D. R.、 RAO K. S.、 RASTOGI K.、 GANDHI S. S.

  DOI：——

  日期：——
• HYPOXIA TARGETED COMPOUNDS FOR CANCER DIAGNOSIS AND THERAPY
  申请人：Das Bhaskar Chandra

  公开号：US20110251189A1

  公开（公告）日：2011-10-13

  The present invention generally relates to oxazine derivative compounds and related compositions and methods for inducing hypoxic tumor cell death, treating cancer and locating a hypoxic tumor in a subject.
• [EN] HYPOXIA TARGETED COMPOUNDS FOR CANCER DIAGNOSIS AND THERAPY<br/>[FR] COMPOSÉS CIBLANT UNE HYPOXIE DESTINÉS AU DIAGNOSTIC ET AU TRAITEMENT D'UN CANCER
  申请人：EINSTEIN COLL MED

  公开号：WO2010068238A1

  公开（公告）日：2010-06-17

  The present invention generally relates to oxazine derivative compounds and related compositions and methods for inducing hypoxic tumor cell death, treating cancer and locating a hypoxic tumor in a subject.