(4-Cyclopropyl-thiazol-2-yl)-acetic acid ethyl ester | 500725-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-Cyclopropyl-thiazol-2-yl)-acetic acid ethyl ester
• 英文别名: Ethyl 2-(4-cyclopropyl-1,3-thiazol-2-yl)acetate
• CAS: 500725-85-9
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: IYQXYSFQURNDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Cyclopropyl-thiazol-2-yl)-acetic acid ethyl ester 在 sodium methylate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3-(4-methoxyphenyl)-1-methyl-5-(4-cyclopropylthiazol-2-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：

  氯甲酸乙酯 、 4-环丙基-2-甲硫基唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 生成 (4-Cyclopropyl-thiazol-2-yl)-acetic acid ethyl ester
  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

• Synthesis and Properties of 3-Substituted 2H-Chromen-2-ones
  作者：I. V. Dyachenko、V. D. Dyachenko、P. V. Dorovatovsky、V. N. Khrustalev、V. G. Nenaidenko

  DOI：10.1134/s1070428020070015

  日期：2020.7

  salicylaldehyde with CH acids [p-methoxyacetoacetanilide, ethyl 3-amino-3-sulfanylidenepropanoate, 3-amino-N-aryl-3-sulfanylidenepropanamides, and ethyl 2-(1,3-thiazol-2- and -4-yl)acetates] afforded 3-substituted chromen-2-ones. Some properties of the products were studied. The structures of 3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2H-chromen-2-one, 2-oxo-2H-chromene-3-carboxamide, and 2-imino-N-(2-metho

  摘要 水杨醛与CH酸[对甲氧基乙酰乙酰苯胺，3-氨基-3-亚磺酰基亚丙酸乙酯，3-氨基-N-芳基-3-亚磺酰基丙酰胺和2-（1,3-噻唑-2-和-4-乙基）乙酸基酯）得到3-取代的铬-2-酮。研究了产品的一些性能。3- [4-（4-氯苯基）-1,3-噻唑-2-基] -2 H-色烯-2-酮，2-氧代-2 H-色烯-3-羧酰胺和2-的结构亚氨基ñ - （2-甲氧基苯基）-2- ħ色烯-3-甲酰胺通过X射线分析测定。
• [EN] TRICYCLIC PYRIDIN-2-ONE ANALOGUES AS LIGANDS FOR GABA-A RECEPTORS<br/>[FR] ANALOGUES DE PYRIDIN-2-ONE TRICYCLIQUE, UTILISES EN TANT QUE LIGANDS POUR RECEPTEURS GABA-A
  申请人：MERCK SHARP & DOHME

  公开号：WO2003018546A2

  公开（公告）日：2003-03-06

  A class of selectively substituted fused tricyclic compounds based on a substituted pyridinone moiety are potent and functionally selective ligands for the α2/α3 subunit of the human GABA-A receptor and are thereby effective in the treatment of anxiety.