N-(1-Methylethyl)-5,6-diphenyl-N-[4-(2H-tetrazol-5-ylmethoxy)butyl]-2-pyrazinamine | 952091-67-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-Methylethyl)-5,6-diphenyl-N-[4-(2H-tetrazol-5-ylmethoxy)butyl]-2-pyrazinamine
• 英文别名: 5,6-diphenyl-N-propan-2-yl-N-[4-(2H-tetrazol-5-ylmethoxy)butyl]pyrazin-2-amine
• CAS: 952091-67-7
• 化学式: C₂₅H₂₉N₇O
• 分子量: 443.552
• InChiKey: XZEVPWJVZOFDGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}acetonitrile 在 sodium azide 、 ammonium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以62%的产率得到N-(1-Methylethyl)-5,6-diphenyl-N-[4-(2H-tetrazol-5-ylmethoxy)butyl]-2-pyrazinamine
  参考文献：
  名称：

  Structure–activity studies on diphenylpyrazine derivatives: A novel class of prostacyclin receptor agonists

  摘要：

  To develop nonprostanoid prostacyclin receptor agonists with a high degree of metabolic resistance and an extended duration of action, a novel series of diphenylpyrazine derivatives was synthesized and evaluated for their inhibition of ADP-induced human platelet aggregation. Structure-activity relationship studies on the side chain containing the carboxylic acid moiety of the lead compound 5c showed that the length of the linker and the presence of the concatenating nitrogen atom adjacent to the pyrazine ring are critical for the antiaggregatory activity. This study led to the discovery of 2-amino-5,6-diphenylpyrazine derivatives 8c, 15a, and 15b. which showed potent inhibition of platelet aggregation with IC50 values of 0.2 mu M. Among these compounds, 15b is an orally available and long-lasting prostacyclin receptor agonist which is promising for the treatment of various vascular diseases. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.010

文献信息

• Structure–activity studies on diphenylpyrazine derivatives: A novel class of prostacyclin receptor agonists
  作者：Tetsuo Asaki、Taisuke Hamamoto、Yukiteru Sugiyama、Keiichi Kuwano、Kenji Kuwabara

  DOI：10.1016/j.bmc.2007.08.010

  日期：2007.11

  To develop nonprostanoid prostacyclin receptor agonists with a high degree of metabolic resistance and an extended duration of action, a novel series of diphenylpyrazine derivatives was synthesized and evaluated for their inhibition of ADP-induced human platelet aggregation. Structure-activity relationship studies on the side chain containing the carboxylic acid moiety of the lead compound 5c showed that the length of the linker and the presence of the concatenating nitrogen atom adjacent to the pyrazine ring are critical for the antiaggregatory activity. This study led to the discovery of 2-amino-5,6-diphenylpyrazine derivatives 8c, 15a, and 15b. which showed potent inhibition of platelet aggregation with IC50 values of 0.2 mu M. Among these compounds, 15b is an orally available and long-lasting prostacyclin receptor agonist which is promising for the treatment of various vascular diseases. (C) 2007 Elsevier Ltd. All rights reserved.