1-(2-羟基-6-甲氧基-3-硝基苯基)乙酮 | 38226-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-羟基-6-甲氧基-3-硝基苯基)乙酮
• 英文名称: 1-(2-hydroxy-6-methoxy-3-nitro-phenyl)-ethanone
• 英文别名: 1-(2-Hydroxy-6-methoxy-3-nitro-phenyl)-aethanon；1-(2-Hydroxy-6-methoxy-3-nitrophenyl)ethanone
• CAS: 38226-01-6
• 化学式: C₉H₉NO₅
• mdl: MFCD00100634
• 分子量: 211.174
• InChiKey: FIVNXYODPHPCLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-6-甲氧基-3-硝基苯基)乙酮 在 硫酸 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 反应 24.0h， 生成 5-methoxy-4',8-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
• 作为产物：
  描述：

  1-(2-羟基-6-甲氧基苯基)乙基-1-酮 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 生成 1-(2-羟基-6-甲氧基-3-硝基苯基)乙酮
  参考文献：
  名称：

  Krause,G.H.; Hoyer,H., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1972, vol. 27, p. 663 - 674

  摘要：

  DOI：

文献信息

• Dalvi; Jadhav, Journal of the Indian Chemical Society, 1957, vol. 34, p. 324
  作者：Dalvi、Jadhav

  DOI：——

  日期：——
• Krause,G.H.; Hoyer,H., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1972, vol. 27, p. 663 - 674
  作者：Krause,G.H.、Hoyer,H.

  DOI：——

  日期：——
• Joshi et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 59,61, 63
  作者：Joshi et al.

  DOI：——

  日期：——
• Naik et al., Proceedings - Indian Academy of Sciences, Section A, 1953, vol. 37, p. 765,768
  作者：Naik et al.

  DOI：——

  日期：——
• Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src
  作者：Mark Cushman、Helen Zhu、Robert L. Geahlen、Alan J. Kraker

  DOI：10.1021/jm00046a020

  日期：1994.9

  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.