N-methyl-2-(4-methyl-2-thienyl)acetamide | 216970-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-methyl-2-(4-methyl-2-thienyl)acetamide
• 英文别名: N-methyl-4-methylthien-2-ylacetamide；N-methyl-2-(4-methylthiophen-2-yl)acetamide
• CAS: 216970-99-9
• 化学式: C₈H₁₁NOS
• 分子量: 169.247
• InChiKey: XZFIFTXVCRGSLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-2-(4-methoxyphenyl)-1-(pyridin-4-yl)propen-1-one 、 N-methyl-2-(4-methyl-2-thienyl)acetamide 生成 3-(4-methoxyphenyl)-1-methyl-5-(4-methylthiophen-2-yl)-1H-[2,4']bipyridinyl-6-one
  参考文献：
  名称：

  Substituted 1H-pyridinyl-2-ones as GABAA alpha 2/3 ligands

  摘要：

  根据式（I）的化合物或其盐是选择性的GABAA受体配体，用于治疗中枢神经系统疾病。

  公开号：

  US06352994B2
• 作为产物：
  描述：

  3-甲基噻吩 、 N,N-二甲基甲酰胺 、 甲胺 、 甲基甲基硫代甲砜 生成 N-methyl-2-(4-methyl-2-thienyl)acetamide 、 N-methyl-2-(3-methyl-2-thienyl)acetamide
  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：US06352994B2

  公开（公告）日：2002-03-05

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

  根据式（I）的化合物或其盐是选择性的GABAA受体配体，用于治疗中枢神经系统疾病。
• 3-Heteroaryl-2-pyridones:  Benzodiazepine Site Ligands with Functional Selectivity for α2/α3-Subtypes of Human GABA_A Receptor-Ion Channels
  作者：Ian Collins、Christopher Moyes、William B. Davey、Michael Rowley、Frances A. Bromidge、Kathleen Quirk、John R. Atack、Ruth M. McKernan、Sally-Ann Thompson、Keith Wafford、Gerard R. Dawson、Andrew Pike、Bindi Sohal、Nancy N. Tsou、Richard G. Ball、José L. Castro

  DOI：10.1021/jm0110789

  日期：2002.4.1

  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.