3-(dimethylamino)-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one | 216970-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(dimethylamino)-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one
• 英文别名: 3-Dimethylamino-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one；3-(dimethylamino)-2-(4-methoxyphenyl)-1-pyridin-4-ylprop-2-en-1-one
• CAS: 216970-76-2
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: KSAPRCRCOQPKCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one 在 4 A molecular sieve 、 盐酸羟胺 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 3-(4-Methoxy-phenyl)-1-methyl-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-1H-[2,4']bipyridinyl-6-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
• 作为产物：
  描述：

  1-isonicotinoyl-1H-imidazole 在 sodium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.33h， 生成 3-(dimethylamino)-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-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

• Substituted 1H-pyridinyl-2-ones as GABAA alpha 2/3 ligands
  申请人：MERCK SHARP & DOHME LIMITED

  公开号：US20010018438A1

  公开（公告）日：2001-08-30

  Compounds according to Formula (I) or a salt thereof are selective ligands for GABA A receptors useful for treatment of disorders of the central nervous system: 1

  根据式(I)或其盐合物的化合物是选择性的GABAA受体配体，可用于治疗中枢神经系统疾病。
• Substituted 1H-pyridinyl-2-ones as GABAA-&agr; 2/3 ligands
  申请人：Merck & Dohme Limited

  公开号：US06200982B1

  公开（公告）日：2001-03-13

  Substituted 1H-Pyridinyl-2-ones are useful as GABAA-Alpha 2/3 ligands.

  替代的1H-吡啶基-2-酮可用作GABAA-Alpha 2/3配体。