5-溴-1-(2,6-二氟苄基)尿嘧啶 | 352304-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-1-(2,6-二氟苄基)尿嘧啶
• 英文名称: 5-bromo-1-(2,6-difluorobenzyl)uracil
• 英文别名: 5-Bromo-1-[(2,6-difluorophenyl)methyl]pyrimidine-2,4-dione
• CAS: 352304-09-7
• 化学式: C₁₁H₇BrF₂N₂O₂
• 分子量: 317.09
• InChiKey: HRQXDXCTWUTAMB-UHFFFAOYSA-N

物化性质

• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-溴-1-(2,6-二氟苄基)尿嘧啶 在 四(三苯基膦)钯 、 sodium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 {(R)-2-[5-(2-Chloro-phenyl)-3-(2,6-difluoro-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：

  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
• 作为产物：
  描述：

  5-溴尿嘧啶 、 2,6-二氟溴苄 在 N,O-双三甲硅基乙酰胺 作用下， 以 1,1-二氯乙烷 为溶剂， 以50%的产率得到5-溴-1-(2,6-二氟苄基)尿嘧啶
  参考文献：
  名称：

  Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

  摘要：

  GnRH受体拮抗剂被披露，可用于治疗男性和女性的各种与性激素相关的疾病。本发明的化合物具有以下结构：其中A、Q、R1、R2、R3a、R3b、R4、R5、R6和n的定义如本文所述，包括立体异构体、前药和其药用可接受盐。还披露了含有本发明化合物与药用可接受载体结合的组合物，以及与使用这些组合物拮抗需要的受试者中的促性腺激素释放激素相关的方法。

  公开号：

  US20020132820A1

文献信息

• Gonadotropin Releasing Hormone Receptor Antagonist, Preparation Method Thereof And Pharmaceutical Composition Comprising The Same
  申请人：Kim Seon Mi

  公开号：US20130137661A1

  公开（公告）日：2013-05-30

  Disclosed are compounds useful as gonadotrophin-releasing hormone (“GnRH”) receptor antagonist.

  披露了作为促性腺激素释放激素（“GnRH”）受体拮抗剂有用的化合物。
• URACIL DERIVATIVES AND USE THEREOF
  申请人：Fahrig Rudolf

  公开号：US20110166096A1

  公开（公告）日：2011-07-07

  Disclosed are uracil derivatives of the formula (I): wherein R 1 , R 2 , R 3 , and X are as defined herein, and use thereof as therapeutic agents. The uracil derivatives are used in particular together with a cytostatic agent for suppressing or reducing resistance building up on cytostatic treatment.

  揭示了以下公式(I)中的尿嘧啶衍生物：其中R1、R2、R3和X如本文所定义，并且其用作治疗剂。尿嘧啶衍生物特别是与细胞毒性药物一起使用，以抑制或减少在细胞毒性治疗中产生的耐药性。
• Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US20020132820A1

  公开（公告）日：2002-09-19

  GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: 1 wherein A, Q, R 1 , R 2 , R 3a , R 3b , R 4 , R 5 , R 6 and n are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.

  GnRH受体拮抗剂被披露，可用于治疗男性和女性的各种与性激素相关的疾病。本发明的化合物具有以下结构：其中A、Q、R1、R2、R3a、R3b、R4、R5、R6和n的定义如本文所述，包括立体异构体、前药和其药用可接受盐。还披露了含有本发明化合物与药用可接受载体结合的组合物，以及与使用这些组合物拮抗需要的受试者中的促性腺激素释放激素相关的方法。
• GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS, MANUFACTURING METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
  申请人：Sk Chemicals Co., Ltd.

  公开号：EP2390250B1

  公开（公告）日：2015-08-12
• Identification of 1-Arylmethyl-3- (2-aminoethyl)-5-aryluracil as Novel Gonadotropin-Releasing Hormone Receptor Antagonists
  作者：Yun-Fei Zhu、Timothy D. Gross、Zhiqiang Guo、Patrick J. Connors,、Yinghong Gao、Fabio C. Tucci、R. Scott Struthers、Greg J. Reinhart、John Saunders、Ta Kung Chen、Anne L. Killam Bonneville、Chen

  DOI：10.1021/jm034041s

  日期：2003.5.1

  Based on SAR from hicyclic GnRH antagonists such as 6-aminomethyl-7-arylpyrrolo[1,2-a]pyrimid-4-ones (1) and 2-aryl-3-aminomethylimidazolo[1,2-a]pyrimid-5-ones (2a,b), a series of novel uracil compounds (4) were derived as the GnRH antagonists. Their syntheses and initial SAR are discussed herein. This is the first time that monocycle-based GnRH receptor antagonists are reported.