6,4'-Dinitroflavone | 158555-11-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6,4'-Dinitroflavone
• 英文别名: 6-Nitro-2-(4-nitro-phenyl)-chromen-4-one；6-nitro-2-(4-nitrophenyl)chromen-4-one
• CAS: 158555-11-4
• 化学式: C₁₅H₈N₂O₆
• 分子量: 312.238
• InChiKey: FPLQIUAPEQSTCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：

  6,4'-Dinitroflavone 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 4',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：

  4'-nitroflavone 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以90%的产率得到6,4'-Dinitroflavone
  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

文献信息

• Regioselective 3-Nitration of Flavones: A New Synthesis of 3-Nitro- and 3-Aminoflavones
  作者：Artur Silva、Diana Patoilo、José Cavaleiro

  DOI：10.1055/s-0029-1219838

  日期：2010.6

  A new, general, and regioselective method for the 3-nitration of flavones have been developed. The nitration reaction is solvent dependent, proceeds via a nitro radical pathway, and the corresponding 3-nitroflavones have been obtained in moderate to very good yields (up to 81%). The reduction of 3-nitroflavones allowed the preparation of the corresponding 3-aminoflavones in very good yields (up to 96%).

  我们开发了一种新的、通用的、具有区域选择性的黄酮 3-硝化方法。硝化反应依赖于溶剂，通过硝基自由基途径进行，相应的 3-硝基黄酮以中等到非常好的收率（高达 81%）获得。通过还原 3-硝基黄酮，可以制备相应的 3-氨基黄酮，收率非常高（高达 96%）。
• Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
  作者：Mariel Marde、Juan Zinczuk、María I. Colombo、Cristina Wasowski、Haydee Viola、Claudia Wolfman、Jorge H. Medina、Edmundo A. Rúveda、Alejandro C. Paladini

  DOI：10.1016/s0960-894x(97)00343-0

  日期：1997.8

  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.
• 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
• US6080780A
  申请人：——

  公开号：US6080780A

  公开（公告）日：2000-06-27
• [EN] USE OF NITROFLAVONOIDS FOR THE TREATMENT OF ANXIETY<br/>[FR] UTILISATION DE NITROFLAVONOIDES POUR TRAITER L'ANXIETE
  申请人：UNIVERSITY OF STRATHCLYDE

  公开号：WO1997014414A1

  公开（公告）日：1997-04-24

  (EN) Methods of treating anxiety with flavonoid compounds according to Formula (I) and dimers thereof, compounds of Formula (I) and dimers thereof, use of compounds of Formula (I) and pharmaceutical formulations comprising flavonoids of Formula (I) and dimers thereof.(FR) Procédés de traitement de l'anxiété au moyen de composés de flavonoïdes selon la formule (I) et de leurs dimères, composés représentés par la formule (I) et leurs dimères, utilisation de composés représentés par la formule (I) et formulations pharmaceutiques comprenant des flavonoïdes de formule (I) et leurs dimères.