[4-(Pyridine-3-carbothioyl)-piperazin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone | 143210-57-5

• 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: [4-(Pyridine-3-carbothioyl)-piperazin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone
• 英文别名: [4-(Pyridine-3-carbothioyl)-piperazin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone; hydrochloride; hydrate；[4-(pyridine-3-carbothioyl)piperazin-1-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 143210-57-5
• 化学式: C₂₀H₂₃N₃O₄S
• 分子量: 401.486
• InChiKey: YJUUUHBJAOQJJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 1-(3,4,5-trimethoxybenzoyl)piperazine 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到[4-(Pyridine-3-carbothioyl)-piperazin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone
  参考文献：
  名称：

  (Pyridylcyanomethyl)piperazines as orally active PAF antagonists

  摘要：

  A series of (pyridylcyanomethyl)piperazines was prepared and evaluated for PAF-antagonist activity. Compounds were tested in vitro in a PAF-induced platelet aggregation assay and in vivo in a PAF-induced hypotension test in normotensive rats. Oral activity was ascertained through a PAF-induced mortality test in mice. The main structure-activity trends of the series were established. Activity was mainly found in four skeletons: 1-acyl-4-(3-pyridylcyanomethyl)-piperazine, 1-acyl-4-(4-pyridylcyanomethyl)piperazine, 1-acyl-4-(3-pyridylcyanomethyl)piperidine, and 1-acyl-4-cyano-4-(3-pyridylamino)piperidine. The acyl substituents, diphenylacetyl and 3,3-diphenylpropionyl, provided the most active compounds, and the introduction of an amine or hydroxy group in the 3,3-diphenylpropionyl substituent led to further improvement in oral activity. As a result, three of the most active compounds (100, 114, and 115) have been selected for further pharmacological development.

  DOI：

  10.1021/jm00100a018

文献信息

• (Pyridylcyanomethyl)piperazines as orally active PAF antagonists
  作者：Elena Carceller、Carmen Almansa、Manuel Merlos、Marta Giral、Javier Bartroli、Julian Garcia-Rafanell、Javier Forn

  DOI：10.1021/jm00100a018

  日期：1992.10

  A series of (pyridylcyanomethyl)piperazines was prepared and evaluated for PAF-antagonist activity. Compounds were tested in vitro in a PAF-induced platelet aggregation assay and in vivo in a PAF-induced hypotension test in normotensive rats. Oral activity was ascertained through a PAF-induced mortality test in mice. The main structure-activity trends of the series were established. Activity was mainly found in four skeletons: 1-acyl-4-(3-pyridylcyanomethyl)-piperazine, 1-acyl-4-(4-pyridylcyanomethyl)piperazine, 1-acyl-4-(3-pyridylcyanomethyl)piperidine, and 1-acyl-4-cyano-4-(3-pyridylamino)piperidine. The acyl substituents, diphenylacetyl and 3,3-diphenylpropionyl, provided the most active compounds, and the introduction of an amine or hydroxy group in the 3,3-diphenylpropionyl substituent led to further improvement in oral activity. As a result, three of the most active compounds (100, 114, and 115) have been selected for further pharmacological development.