Hexanoic acid (4,6-diphenyl-pyrimidin-2-yl)-amide | 820961-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Hexanoic acid (4,6-diphenyl-pyrimidin-2-yl)-amide
• 英文别名: N-(4,6-diphenylpyrimidin-2-yl)hexanamide
• CAS: 820961-67-9
• 化学式: C₂₂H₂₃N₃O
• mdl: MFCD14827861
• 分子量: 345.444
• InChiKey: LZYGCRHBKZGRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,6-二苯基-2-氨基嘧啶 、 己酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到Hexanoic acid (4,6-diphenyl-pyrimidin-2-yl)-amide
  参考文献：
  名称：

  2,4,6-Trisubstituted Pyrimidines as a New Class of Selective Adenosine A₁ Receptor Antagonists

  摘要：

  Adenosine receptor antagonists usually possess a bi- or tricyclic heteroaromatic structure at their core with varying substitution patterns to achieve selectivity and/or greater affinity. Taking into account molecular modeling results from a series of potent adenosine A(1) receptor antagonists, a pharmacophore was derived from which we show that a monocyclic core can be equally effective. To achieve a compound that may act at the GNS we propose imposing a restriction related to its polar surface area (PSA). In consequence, we have synthesized two novel series of pyrimidines, possessing good potency at the adenosine A, receptor and desirable PSA values. In particular, compound 30 (LUF 5735) displays excellent A, affinity (K-i = 4 nM) and selectivity (less than or equal to50% displacement of 1 muM concentrations of the radioligand at the other three adenosine receptors) and has a PSA value of 53 Angstrom2.

  DOI：

  10.1021/jm049448r

文献信息

• 2,4,6-Trisubstituted Pyrimidines as a New Class of Selective Adenosine A₁ Receptor Antagonists
  作者：Lisa C. W. Chang、Ronald F. Spanjersberg、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Gijs van den Hout、Margot W. Beukers、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm049448r

  日期：2004.12.1

  Adenosine receptor antagonists usually possess a bi- or tricyclic heteroaromatic structure at their core with varying substitution patterns to achieve selectivity and/or greater affinity. Taking into account molecular modeling results from a series of potent adenosine A(1) receptor antagonists, a pharmacophore was derived from which we show that a monocyclic core can be equally effective. To achieve a compound that may act at the GNS we propose imposing a restriction related to its polar surface area (PSA). In consequence, we have synthesized two novel series of pyrimidines, possessing good potency at the adenosine A, receptor and desirable PSA values. In particular, compound 30 (LUF 5735) displays excellent A, affinity (K-i = 4 nM) and selectivity (less than or equal to50% displacement of 1 muM concentrations of the radioligand at the other three adenosine receptors) and has a PSA value of 53 Angstrom2.