5-Cyano-2-hydroxy-3-nitro-acetophenon | 70978-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Cyano-2-hydroxy-3-nitro-acetophenon
• 英文别名: 3-Acetyl-4-hydroxy-5-nitrobenzonitrile
• CAS: 70978-59-5
• 化学式: C₉H₆N₂O₄
• 分子量: 206.158
• InChiKey: POSRSUVIZIUNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Cyano-2-hydroxy-3-nitro-acetophenon 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以65%的产率得到3-乙酰基-5-氨基-4-羟基苯甲腈
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides

  摘要：

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.

  DOI：

  10.1021/jm00154a019
• 作为产物：
  描述：

  2-乙酰基-4-氰基苯酚 在 硫酸 、 硝酸 作用下， 以59%的产率得到5-Cyano-2-hydroxy-3-nitro-acetophenon
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides

  摘要：

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.

  DOI：

  10.1021/jm00154a019

文献信息

• DE2846931
  申请人：——

  公开号：——

  公开（公告）日：——
• FORD, E.;KNOWLES, PH.;LUNT, E.;MARSHALL, S. M.;PENROSE, A. J.;RAMSDEN, A.+, J. MED. CHEM., 1986, 29, N 4, 538-549
  作者：FORD, E.、KNOWLES, PH.、LUNT, E.、MARSHALL, S. M.、PENROSE, A. J.、RAMSDEN, A.+

  DOI：——

  日期：——
• US4442115A
  申请人：——

  公开号：US4442115A

  公开（公告）日：1984-04-10
• Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides
  作者：Roger E. Ford、Phillip Knowles、Edward Lunt、Stuart M. Marshall、Audrey J. Penrose、Christopher A. Ramsden、Anthony J. H. Summers、Joyce L. Walker、Derek E. Wright

  DOI：10.1021/jm00154a019

  日期：1986.4

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.