2-(1-methyl-1-hydroxycarbonylethyl)-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-one | 528859-36-1

• 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: 2-(1-methyl-1-hydroxycarbonylethyl)-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-one
• 英文别名: 2-[8-[(2-Fluorophenyl)methyl]-6-(3-methoxyphenyl)-7-methyl-5-oxoimidazo[1,2-a]pyrimidin-2-yl]-2-methylpropanoic acid
• CAS: 528859-36-1
• 化学式: C₂₅H₂₄FN₃O₄
• 分子量: 449.482
• InChiKey: IGPOATLLDFMWAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-1-hydroxycarbonylethyl)-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以69%的产率得到2-(1,1-dimethyl-2-hydroxy)ethyl-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-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
• 作为产物：
  描述：

  2-(1-methyl-1-methoxycarbonylethyl)-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到2-(1-methyl-1-hydroxycarbonylethyl)-6-(3-methoxyphenyl)-7-methyl-8-(2-fluorobenzyl)imidazolo[1,2-a]pyrimid-5-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

• 8-SUBSTITUTED IMIDAZOPYRIMIDINONE DERIVATIVE HAVING AUTOTAXIN INHIBITORY ACTIVITY
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20160002247A1

  公开（公告）日：2016-01-07

  A compound of formula (I) wherein variables are as defined herein having an autotaxin inhibitory effect and a pharmaceutical composition comprising the same.

  具有自体脂肪酶抑制作用的化合物（I）的化学式，其中变量如本文所定义，并且包含该化合物的药物组合物。
• 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.