2-(4-methoxyphenyl)-1-(4-dimethylaminophenyl)ethan-1-one | 97606-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-methoxyphenyl)-1-(4-dimethylaminophenyl)ethan-1-one
• 英文别名: 1-[4-(Dimethylamino)phenyl]-2-(4-methoxyphenyl)ethanone
• CAS: 97606-30-9
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: IATQKNCFMFBDLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-1-(4-dimethylaminophenyl)ethan-1-one 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 6-(4-Dimethylamino-phenyl)-5-(4-methoxy-phenyl)-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  3-Heteroaryl-2-pyridones:  Benzodiazepine Site Ligands with Functional Selectivity for α2/α3-Subtypes of Human GABA_A Receptor-Ion Channels

  摘要：

  A novel series of 3-heteroaryl-5,6-bis(aryl)-1-methyl-2-pyridones were developed with high affinity for the benzodiazepine (BZ) binding site of human gamma-aminobutyric acid (GABA(A)) receptor ion channels, low binding selectivity for alpha2- and/or alpha3- over alpha1-containing GABA(A) receptor subtypes and high binding selectivity over alpha5 subtypes. High affinity appeared to be associated with a coplanar conformation of the pyridone and sulfur-containing 3-heteroaryl rings resulting from an attractive S...O intramolecular interaction. Functional selectivity (i.e., selective efficacy) for alpha2 and/or alpha3 GABA(A) receptor subtypes over alpha1 was observed in several of these compounds in electrophysiological assays. Furthermore, an alpha3 subtype selective inverse agonist was proconvulsant and anxiogenic in rodents while an alpha2/alpha3 subtype selective partial agonist was anticonvulsant and anxiolytic, supporting the hypothesis that subtype selective BZ site agonists may provide new anxiolytic therapies.

  DOI：

  10.1021/jm0110789
• 作为产物：
  描述：

  2-(4-(dimethylamino)phenyl)-2-((trimethylsilyl)oxy)acetonitrile 在 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 36.5h， 生成 2-(4-methoxyphenyl)-1-(4-dimethylaminophenyl)ethan-1-one
  参考文献：
  名称：

  3-Heteroaryl-2-pyridones:  Benzodiazepine Site Ligands with Functional Selectivity for α2/α3-Subtypes of Human GABA_A Receptor-Ion Channels

  摘要：

  A novel series of 3-heteroaryl-5,6-bis(aryl)-1-methyl-2-pyridones were developed with high affinity for the benzodiazepine (BZ) binding site of human gamma-aminobutyric acid (GABA(A)) receptor ion channels, low binding selectivity for alpha2- and/or alpha3- over alpha1-containing GABA(A) receptor subtypes and high binding selectivity over alpha5 subtypes. High affinity appeared to be associated with a coplanar conformation of the pyridone and sulfur-containing 3-heteroaryl rings resulting from an attractive S...O intramolecular interaction. Functional selectivity (i.e., selective efficacy) for alpha2 and/or alpha3 GABA(A) receptor subtypes over alpha1 was observed in several of these compounds in electrophysiological assays. Furthermore, an alpha3 subtype selective inverse agonist was proconvulsant and anxiogenic in rodents while an alpha2/alpha3 subtype selective partial agonist was anticonvulsant and anxiolytic, supporting the hypothesis that subtype selective BZ site agonists may provide new anxiolytic therapies.

  DOI：

  10.1021/jm0110789

文献信息

• 5-(aryl and heteroaryl)-6-(aryl and heteroaryl)-1,2-dihydro-2-oxo 3-pyridinecarboxylic acids and derivatives thereof
  申请人：Merck & Co., Inc.

  公开号：EP0308020A2

  公开（公告）日：1989-03-22

  This invention relates to a method of treating bacterial infections with 5-(aryl and heteroaryl)-6-(aryl and heteroaryl)-1,2-dihydro-2-oxo-­3-pyridinecarboxylic acids and derivatives thereof. This invention further relates to pharmaceutical compositions that are useful in the treatment of bacterial infections.

  本发明涉及一种用 5-(芳基和杂芳基)-6-(芳基和杂芳基)-1,2-二氢-2-氧代-3-吡啶甲酸及其衍生物治疗细菌感染的方法。本发明还涉及可用于治疗细菌感染的药物组合物。
• Pulst, M.; Weissenfels, M.; Dietz, F., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1985, vol. 40, # 5, p. 585 - 589
  作者：Pulst, M.、Weissenfels, M.、Dietz, F.

  DOI：——

  日期：——
• PULST, M.;WEISSENFELS, M.;DIETZ, F, Z. NATURFORSCH., 1985, 40, N 5, 585-589
  作者：PULST, M.、WEISSENFELS, M.、DIETZ, F

  DOI：——

  日期：——