3-((R)-2-Amino-2-phenyl-ethyl)-5-(2-fluoro-3-hydroxy-phenyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-1H-pyrimidine-2,4-dione | 855230-52-3

• 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-((R)-2-Amino-2-phenyl-ethyl)-5-(2-fluoro-3-hydroxy-phenyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-1H-pyrimidine-2,4-dione
• 英文别名: 3-[(2R)-2-amino-2-phenylethyl]-5-(2-fluoro-3-hydroxyphenyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]pyrimidine-2,4-dione
• CAS: 855230-52-3
• 化学式: C₂₆H₂₀F₅N₃O₃
• 分子量: 517.455
• InChiKey: DMCFVTPQXWWYQE-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-((R)-2-Amino-2-phenyl-ethyl)-5-(2-fluoro-3-hydroxy-phenyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-1H-pyrimidine-2,4-dione 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 {(R)-2-[5-(2-Fluoro-3-hydroxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Zwitterionic uracil derivatives as potent GnRH receptor antagonists with improved pharmaceutical properties

  摘要：

  A novel series of potent zwitterionic uracil GnRH antagonists were discovered that showed reduced liability for CYP3A4 enzyme inhibition. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.059
• 作为产物：
  描述：

  2-氟-6-(三氟甲基)溴苄 在 四(三苯基膦)钯 、 N,O-双三甲硅基乙酰胺 、 sodium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 3-((R)-2-Amino-2-phenyl-ethyl)-5-(2-fluoro-3-hydroxy-phenyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Uracils as potent antagonists of the human gonadotropin-releasing hormone receptor without atropisomers

  摘要：

  Uracil derivatives were designed and synthesized to avoid atropisomers observed in the 6-methyluracils as antagonists of the human GnRH receptor. Optimization at the 1- and 5-positions of the uracil resulted in potent compounds such as 24 (K-i = 0.45 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.057

文献信息

• Uracils as potent antagonists of the human gonadotropin-releasing hormone receptor without atropisomers
  作者：Zhiqiang Guo、Yongsheng Chen、Charles Q. Huang、Timothy D. Gross、Joseph Pontillo、Martin W. Rowbottom、John Saunders、Scott Struthers、Fabio C. Tucci、Qiu Xie、Warren Wade、Yun-Fei Zhu、Dongpei Wu、Chen Chen

  DOI：10.1016/j.bmcl.2005.03.057

  日期：2005.5

  Uracil derivatives were designed and synthesized to avoid atropisomers observed in the 6-methyluracils as antagonists of the human GnRH receptor. Optimization at the 1- and 5-positions of the uracil resulted in potent compounds such as 24 (K-i = 0.45 nM). (c) 2005 Elsevier Ltd. All rights reserved.
• Zwitterionic uracil derivatives as potent GnRH receptor antagonists with improved pharmaceutical properties
  作者：Colin F. Regan、Zhiqiang Guo、Yongsheng Chen、Charles Q. Huang、Mi Chen、Wanlong Jiang、Jaimie K. Rueter、Timothy Coon、Chen Chen、John Saunders、Michael S. Brown、Steve F. Betz、R. Scott Struthers、Chun Yang、Jenny Wen、Ajay Madan、Yun-Fei Zhu

  DOI：10.1016/j.bmcl.2008.07.059

  日期：2008.8

  A novel series of potent zwitterionic uracil GnRH antagonists were discovered that showed reduced liability for CYP3A4 enzyme inhibition. (c) 2008 Elsevier Ltd. All rights reserved.