5-(2-chloro-3-methoxyphenyl)-3-[(2R)-2-(cyclopentylamino)butyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione | 1044526-66-0

• 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: 5-(2-chloro-3-methoxyphenyl)-3-[(2R)-2-(cyclopentylamino)butyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione
• CAS: 1044526-66-0
• 化学式: C₂₉H₃₂ClF₄N₃O₃
• 分子量: 582.038
• InChiKey: FMLZUVLSVOQILD-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 环戊酮 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 5-(2-chloro-3-methoxyphenyl)-3-[(2R)-2-(cyclopentylamino)butyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  5-Aryluracils as potent GnRH antagonists—Characterization of atropisomers

  摘要：

  Optimization of a series of uracils bearing a 2-fluoro-or 2-chloro-3-methoxyphenyl group at the 5-position resulted in compounds such as 3d and 3f with subnanomolar binding affinity at the human GnRH receptor. While the 2-fluoro-3-methoxyphenyl compound 3a was characterized as a mixture of interchangeable atropisomers, the diastereoisomers of 2-chloro-3-methoxyphenyl analogs were separated. It was found that the aR-atropisomer was much more potent than the aS-isomer based on the X-ray crystal structure of 3h-II. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.029

文献信息

• 5-Aryluracils as potent GnRH antagonists—Characterization of atropisomers
  作者：Liren Zhao、Zhiqiang Guo、Yongsheng Chen、Tao Hu、Dongpei Wu、Yun-Fei Zhu、Martin Rowbottom、Timothy D. Gross、Fabio C. Tucci、R. Scott Struthers、Qiu Xie、Chen Chen

  DOI：10.1016/j.bmcl.2008.04.029

  日期：2008.6

  Optimization of a series of uracils bearing a 2-fluoro-or 2-chloro-3-methoxyphenyl group at the 5-position resulted in compounds such as 3d and 3f with subnanomolar binding affinity at the human GnRH receptor. While the 2-fluoro-3-methoxyphenyl compound 3a was characterized as a mixture of interchangeable atropisomers, the diastereoisomers of 2-chloro-3-methoxyphenyl analogs were separated. It was found that the aR-atropisomer was much more potent than the aS-isomer based on the X-ray crystal structure of 3h-II. (C) 2008 Elsevier Ltd. All rights reserved.