N-<<4-(tetradecyloxy)phenyl>methyl>-2-pyridinecarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-<<4-(tetradecyloxy)phenyl>methyl>-2-pyridinecarboxamide
• 英文别名: N-[(4-tetradecoxyphenyl)methyl]pyridine-2-carboxamide
• 化学式: C₂₇H₄₀N₂O₂
• 分子量: 424.627
• InChiKey: AZXYJEQZQJQYCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸乙酯 、 N-<<4-(tetradecyloxy)phenyl>methyl>-2-pyridinecarboxamide 以 甲苯 为溶剂， 生成 1-ethyl-N-[(4-tetradecoxyphenyl)methyl]pyridin-1-ium-2-carboxamide;trifluoromethanesulfonate
  参考文献：
  名称：

  Analogs of platelet activating factor. 8. Antagonists of PAF containing an aromatic ring linked to a pyridinium ring

  摘要：

  A series of platelet activating factor (PAF) antagonists containing a quaternary pyridinium ring connected through an amide, imide, or carbamate linkage to a substituted aromatic ring was prepared. Of these compounds, those containing a branched imide linkage of the form (CON-(COCH3)CH2, 37-51, and 59) generally showed excellent PAF antagonist properties in vitro. Structure-activity relationships within this series of compounds were studied extensively with respect to substituents and the position of substitution in both the aromatic and pyridinium rings. Several of these compounds (40 and 44) showed in vitro PAF antagonism at less than 0.1 muM and are as potent as CV-6209, the most potent PAF antagonist reported in the literature. Less active PAF antagonists were those bearing simple amide linkages (20-23, 27-29, and 31-35), linear imide linkages (62-63), or carbamate linkages (66 and 68), between the two aromatic rings. A number of our PAF antagonists were tested in vivo in mice and rabbits for their ability to protect these animals against a lethal injection of PAF. Those antagonists that are particularly potent (IC50 <0.1 muM) provide excellent protection against an LD97 dose of PAF in rabbits. The relationships between structure and activity in vitro and in vivo are presented and compared to literature standards.

  DOI：

  10.1021/jm00057a008
• 作为产物：
  描述：

  吡啶-2-甲酰氯盐酸盐 、 4-(tetradecyloxy)benzenemethanamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到N-<<4-(tetradecyloxy)phenyl>methyl>-2-pyridinecarboxamide
  参考文献：
  名称：

  Analogs of platelet activating factor. 8. Antagonists of PAF containing an aromatic ring linked to a pyridinium ring

  摘要：

  A series of platelet activating factor (PAF) antagonists containing a quaternary pyridinium ring connected through an amide, imide, or carbamate linkage to a substituted aromatic ring was prepared. Of these compounds, those containing a branched imide linkage of the form (CON-(COCH3)CH2, 37-51, and 59) generally showed excellent PAF antagonist properties in vitro. Structure-activity relationships within this series of compounds were studied extensively with respect to substituents and the position of substitution in both the aromatic and pyridinium rings. Several of these compounds (40 and 44) showed in vitro PAF antagonism at less than 0.1 muM and are as potent as CV-6209, the most potent PAF antagonist reported in the literature. Less active PAF antagonists were those bearing simple amide linkages (20-23, 27-29, and 31-35), linear imide linkages (62-63), or carbamate linkages (66 and 68), between the two aromatic rings. A number of our PAF antagonists were tested in vivo in mice and rabbits for their ability to protect these animals against a lethal injection of PAF. Those antagonists that are particularly potent (IC50 <0.1 muM) provide excellent protection against an LD97 dose of PAF in rabbits. The relationships between structure and activity in vitro and in vivo are presented and compared to literature standards.

  DOI：

  10.1021/jm00057a008

文献信息

• Analogs of platelet activating factor. 8. Antagonists of PAF containing an aromatic ring linked to a pyridinium ring
  作者：Michael P. Trova、Allan Wissner、Marion L. Carroll、Suresh S. Kerwar、Walter C. Pickett、Robert E. Schaub、Lawrence W. Torley、Constance A. Kohler

  DOI：10.1021/jm00057a008

  日期：1993.3

  A series of platelet activating factor (PAF) antagonists containing a quaternary pyridinium ring connected through an amide, imide, or carbamate linkage to a substituted aromatic ring was prepared. Of these compounds, those containing a branched imide linkage of the form (CON-(COCH3)CH2, 37-51, and 59) generally showed excellent PAF antagonist properties in vitro. Structure-activity relationships within this series of compounds were studied extensively with respect to substituents and the position of substitution in both the aromatic and pyridinium rings. Several of these compounds (40 and 44) showed in vitro PAF antagonism at less than 0.1 muM and are as potent as CV-6209, the most potent PAF antagonist reported in the literature. Less active PAF antagonists were those bearing simple amide linkages (20-23, 27-29, and 31-35), linear imide linkages (62-63), or carbamate linkages (66 and 68), between the two aromatic rings. A number of our PAF antagonists were tested in vivo in mice and rabbits for their ability to protect these animals against a lethal injection of PAF. Those antagonists that are particularly potent (IC50 <0.1 muM) provide excellent protection against an LD97 dose of PAF in rabbits. The relationships between structure and activity in vitro and in vivo are presented and compared to literature standards.