3-[(2R)-2-(cyclopentylamino)propyl]-1-[(2,6-difluorophenyl)methyl]-5-(2-fluoro-3-methoxyphenyl)-6-methylpyrimidine-2,4-dione | 352300-39-1

• 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: 3-[(2R)-2-(cyclopentylamino)propyl]-1-[(2,6-difluorophenyl)methyl]-5-(2-fluoro-3-methoxyphenyl)-6-methylpyrimidine-2,4-dione
• CAS: 352300-39-1
• 化学式: C₂₇H₃₀F₃N₃O₃
• 分子量: 501.549
• InChiKey: XTOLERVEHAIVDS-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  环戊酮 、 3-((R)-2-Amino-propyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(2R)-2-(cyclopentylamino)propyl]-1-[(2,6-difluorophenyl)methyl]-5-(2-fluoro-3-methoxyphenyl)-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.