3',6-二硝基黄酮 | 100914-36-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3',6-二硝基黄酮
• 英文名称: 6,3'-Dinitroflavone
• 英文别名: 6-nitro-2-(3-nitro-phenyl)-chromen-4-one；6-Nitro-2-(3-nitro-phenyl)-chromen-4-on；3',6-Dinitroflavone；6-nitro-2-(3-nitrophenyl)chromen-4-one
• CAS: 100914-36-1
• 化学式: C₁₅H₈N₂O₆
• 分子量: 312.238
• InChiKey: CNVQMRWAJHEFGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',6-二硝基黄酮 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 3',6-diaminoflavone
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src

  摘要：

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.

  DOI：

  10.1021/jm00046a020
• 作为产物：
  描述：

  2-羟基-5-硝基苯乙酮 在 氢氧化钾 、 溴 作用下， 以 吡啶 为溶剂， 生成 3',6-二硝基黄酮
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0

文献信息

• Reichel; Hempel, Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 184,193
  作者：Reichel、Hempel

  DOI：——

  日期：——
• A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation
  作者：Michael Lorenz、M. Shahjahan Kabir、James M. Cook

  DOI：10.1016/j.tetlet.2009.12.107

  日期：2010.2

  A general route for the synthesis of biologically important flavones is reported via a two step sequence employing a catalytic Wacker-Cook oxidation(4b) as the key step. (C) 2009 Elsevier Ltd. All rights reserved.
• USE OF NITROFLAVONOIDS FOR THE TREATMENT OF ANXIETY
  申请人：University of Strathclyde

  公开号：EP0857066A1

  公开（公告）日：1998-08-12
• SEDATIVE MATERIALS AND TREATMENTS
  申请人：University of Strathclyde

  公开号：EP1503771B1

  公开（公告）日：2008-07-23
• US6080780A
  申请人：——

  公开号：US6080780A

  公开（公告）日：2000-06-27