甲酮,苯基-2-嘧啶基-,肟,(E)- | 174813-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 甲酮,苯基-2-嘧啶基-,肟,(E)-
• 英文名称: E-phenyl(2-pyrimidinyl)methanone oxime
• 英文别名: (NE)-N-[phenyl(pyrimidin-2-yl)methylidene]hydroxylamine
• CAS: 174813-06-0
• 化学式: C₁₁H₉N₃O
• 分子量: 199.212
• InChiKey: UAMLLDLQCALQQP-GXDHUFHOSA-N

物化性质

• 沸点：
  421.6±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ethyl 4-[(E)-[phenyl(pyrimidin-2-yl)methylidene]amino]oxybutanoate	180865-38-7	C17H19N3O3	313.356
  ——	ethyl 5-[(E)-[phenyl(pyrimidin-2-yl)methylidene]amino]oxypentanoate	180865-50-3	C18H21N3O3	327.383
  ——	ethyl 6-[(E)-[phenyl(pyrimidin-2-yl)methylidene]amino]oxyhexanoate	180865-62-7	C19H23N3O3	341.41

反应信息

• 作为反应物：
  描述：

  甲酮,苯基-2-嘧啶基-,肟,(E)- 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 25.17h， 生成 4-[1-Phenyl-1-pyrimidin-2-yl-meth-(E)-ylideneaminooxy]-butyric acid
  参考文献：
  名称：

  On the Bioisosteric Potential of Diazines:  Diazine Analogues of the Combined Thromboxane A₂ Receptor Antagonist and Synthetase Inhibitor Ridogrel

  摘要：

  In this SAR study the bioisosteric potential of diazines in the field of combined antithrombotic thromboxane A(2) synthetase inhibitors and receptor antagonists was investigated. In this context, two series of (E)- and (Z)-omega-[[(aryldiazinylmethylene)amino]oxy]alkanoic acids were synthesized of which pentanoic acid derivatives with a 2-pyrazinyl, 4-pyridazinyl, or 6-pyrimidinyl group were found to exhibit this dual activity, while 4-pyrimidinyl as well as 3-pyridazinyl analogues showed only receptor antagonistic activity and 2-pyrimidinyl congeners were inactive. In the series of diazine analogues of Ridogrel (1), replacement of the 3-pyridyl group by a 2-pyrazinyl, 4-pyridazinyl, or 5-pyrimidinyl moiety led to compounds that inhibit thromboxane A(2) synthetase in gel-filtered human platelets comparable to 1 (IC50 Of 0.006, 0.016, and 0.039 mu M, respectively, versus 0.007 mu M) Radioligand-binding studies with [H-3]SQ 29,548 in washed human platelets revealed that these diazine analogues block the thromboxane Az receptor with an IC50 of 11, 6.0, and 1.5 mu M, respectively. This compares well with the IC50 = 1.7 mu M of 1. Finally, testing of inhibition of collagen-induced platelet aggregation in human platelet-rich plasma with 2-pyrazinyl, 4-pyridazinyl, or 5-pyrimidinyl congeners of Ridogrel indicated that these heteroaromatic moieties may serve as bioisosteric substitutes of a 3-pyridyl group in dual-acting antiplatelet agents.

  DOI：

  10.1021/jm960341g
• 作为产物：
  描述：

  2-嘧啶乙酰腈,a-苯基- 在 sodium hydroxide 、 盐酸羟胺 、 苄基三乙基氯化铵 、 sodium acetate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 甲酮,苯基-2-嘧啶基-,肟,(E)-
  参考文献：
  名称：

  Aryl Diazinyl Ketoximes: Synthesis and Configurational Assignment

  摘要：

  Preparation of a series of new aryl diazinyl ketoximes (7a,b - 12a,b) required as synthetic building blocks is described. Separation of the E/Z-isomers obtained was achieved by means of chromatography, their configuration was assigned using nmr techniques. Moreover, procedures for the synthesis of the starting ketones (1b - 6b) are given.

  DOI：

  10.3987/com-95-7248

文献信息

• Aryl Diazinyl Ketoximes: Synthesis and Configurational Assignment
  作者：Gottfried Heinisch、Wolfgang Holzer、Thierry Langer、Peter Lukavsky

  DOI：10.3987/com-95-7248

  日期：——

  Preparation of a series of new aryl diazinyl ketoximes (7a,b - 12a,b) required as synthetic building blocks is described. Separation of the E/Z-isomers obtained was achieved by means of chromatography, their configuration was assigned using nmr techniques. Moreover, procedures for the synthesis of the starting ketones (1b - 6b) are given.
• On the Bioisosteric Potential of Diazines:  Diazine Analogues of the Combined Thromboxane A₂ Receptor Antagonist and Synthetase Inhibitor Ridogrel
  作者：Gottfried Heinisch、Wolfgang Holzer、Friedbert Kunz、Thierry Langer、Peter Lukavsky、Christoph Pechlaner、Hans Weissenberger

  DOI：10.1021/jm960341g

  日期：1996.1.1

  In this SAR study the bioisosteric potential of diazines in the field of combined antithrombotic thromboxane A(2) synthetase inhibitors and receptor antagonists was investigated. In this context, two series of (E)- and (Z)-omega-[[(aryldiazinylmethylene)amino]oxy]alkanoic acids were synthesized of which pentanoic acid derivatives with a 2-pyrazinyl, 4-pyridazinyl, or 6-pyrimidinyl group were found to exhibit this dual activity, while 4-pyrimidinyl as well as 3-pyridazinyl analogues showed only receptor antagonistic activity and 2-pyrimidinyl congeners were inactive. In the series of diazine analogues of Ridogrel (1), replacement of the 3-pyridyl group by a 2-pyrazinyl, 4-pyridazinyl, or 5-pyrimidinyl moiety led to compounds that inhibit thromboxane A(2) synthetase in gel-filtered human platelets comparable to 1 (IC50 Of 0.006, 0.016, and 0.039 mu M, respectively, versus 0.007 mu M) Radioligand-binding studies with [H-3]SQ 29,548 in washed human platelets revealed that these diazine analogues block the thromboxane Az receptor with an IC50 of 11, 6.0, and 1.5 mu M, respectively. This compares well with the IC50 = 1.7 mu M of 1. Finally, testing of inhibition of collagen-induced platelet aggregation in human platelet-rich plasma with 2-pyrazinyl, 4-pyridazinyl, or 5-pyrimidinyl congeners of Ridogrel indicated that these heteroaromatic moieties may serve as bioisosteric substitutes of a 3-pyridyl group in dual-acting antiplatelet agents.