3-[N-methyl-N-(2-pyridylethyl)]aminomethyl-2-(tert-butyl)-6-methyl-7-(2-fluorobenzyl)-5-(3-methoxyphenyl)imidazolo[1,2-a]pyrimid-4-one

• 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: 3-[N-methyl-N-(2-pyridylethyl)]aminomethyl-2-(tert-butyl)-6-methyl-7-(2-fluorobenzyl)-5-(3-methoxyphenyl)imidazolo[1,2-a]pyrimid-4-one
• 英文别名: 8-(2-fluorobenzyl)-2-tert-butyl-6-(3-methoxyphenyl)-7-methyl-3-((methyl(2-(pyridin-2-yl)ethyl)amino)methyl)imidazo[1,2-a]pyrimidin-5(8H)-one；2-tert-butyl-8-[(2-fluorophenyl)methyl]-6-(3-methoxyphenyl)-7-methyl-3-[[methyl(2-pyridin-2-ylethyl)amino]methyl]imidazo[1,2-a]pyrimidin-5-one
• 化学式: C₃₄H₃₈FN₅O₂
• 分子量: 567.706
• InChiKey: AGCGNLBZIDUYNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-溴频哪酮 在 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 3-[N-methyl-N-(2-pyridylethyl)]aminomethyl-2-(tert-butyl)-6-methyl-7-(2-fluorobenzyl)-5-(3-methoxyphenyl)imidazolo[1,2-a]pyrimid-4-one
  参考文献：
  名称：

  Design and Structure−Activity Relationships of 2-Alkyl-3-aminomethyl-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-ones as Potent GnRH Receptor Antagonists

  摘要：

  SAR studies of 7-phenylpyrrolo[1,2-a]pyrimid-4-ones 1 and 2, and 2-phenylimidazolo[1,2-a]-pyrimidines 3 and 4, as nonpeptide human GnRH receptor antagonists, lead us to believe that the aromatic ring at position-2 of 4 is no longer crucial for the binding once an aryl group is incorporated at postion-6. We report here the use of a 2-alkyl group on the imidazolo[1,2-a]-pyrimidone core to generate potent GnRH receptor antagonists. This discovery enabled us to obtain smaller but equally potent GnRH receptor antagonists.

  DOI：

  10.1021/jm0205402

文献信息

• Design and Structure−Activity Relationships of 2-Alkyl-3-aminomethyl-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-<i>a</i>]pyrimid-5-ones as Potent GnRH Receptor Antagonists
  作者：Yun-Fei Zhu、Zhiqiang Guo、Timothy D. Gross、Yinghong Gao、Patrick J. Connors,、R. Scott Struthers、Qiu Xie、Fabio C. Tucci、Greg J. Reinhart、Dongpei Wu、John Saunders、Chen

  DOI：10.1021/jm0205402

  日期：2003.4.1

  SAR studies of 7-phenylpyrrolo[1,2-a]pyrimid-4-ones 1 and 2, and 2-phenylimidazolo[1,2-a]-pyrimidines 3 and 4, as nonpeptide human GnRH receptor antagonists, lead us to believe that the aromatic ring at position-2 of 4 is no longer crucial for the binding once an aryl group is incorporated at postion-6. We report here the use of a 2-alkyl group on the imidazolo[1,2-a]-pyrimidone core to generate potent GnRH receptor antagonists. This discovery enabled us to obtain smaller but equally potent GnRH receptor antagonists.