ethyl 2-(fluoromethyl)-6-oxo-1H-pyrimidine-5-carboxylate | 308143-20-6

• 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: ethyl 2-(fluoromethyl)-6-oxo-1H-pyrimidine-5-carboxylate
• CAS: 308143-20-6
• 化学式: C₈H₉FN₂O₃
• 分子量: 200.169
• InChiKey: DKSUQOKINGJODU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(fluoromethyl)-6-oxo-1H-pyrimidine-5-carboxylate 在 四丁基氟化铵 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 21.0h， 生成 3-fluoro-4-(2-fluorobenzyl)2-[4-(2-methylpropyloxy)phenyl]-6-(ethyloxycarbonyl)pyrrolo[1,2-a]pyrimid-7-one
  参考文献：
  名称：

  A novel synthesis of 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones as potent, stable GnRH receptor antagonists

  摘要：

  A new class of small molecule GnRH antagonists, the 7-aryl-8-fluoro-pyrrolo[1,2-a]pyrimid-4-ones, was designed and a novel synthesis for these compounds was developed. The synthesis utilizes a base-catalyzed intramolecular cyclization of fluoromethyl pyrimidone 5 to generate the bicyclic core. Amongst the compounds synthesized, we discovered some highly potent GnRH receptor antagonists (e.g., 12. K-i = 9 nM), which showed enhanced stability towards acidic physiological conditions compared to the des-fluoro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00745-x
• 作为产物：
  描述：

  α-fluoroacetamide hydrochloride 、 乙氧基甲叉丙二酸二乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以26%的产率得到ethyl 2-(fluoromethyl)-6-oxo-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

  摘要：

  GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。该发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中Ar、B、R1、R2、R3a、R3b、R4、R5、R6和m的定义如本文所述。

  公开号：

  US06346534B1

文献信息

• PESTICIDAL COMPOSITIONS
  申请人：Nugent Benjamin M.

  公开号：US20100056534A1

  公开（公告）日：2010-03-04

  Pesticide compositions and their use in controlling pests are provided.

  提供了杀虫剂组合物及其在控制害虫方面的使用。
• Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
  申请人：Neurocrine Biosciences, Inc.

  公开号：US06346534B1

  公开（公告）日：2002-02-12

  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: including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6 and m are as defined herein.

  GnRH受体拮抗剂已被披露，可用于治疗男性和女性的各种与性激素相关的疾病。该发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中Ar、B、R1、R2、R3a、R3b、R4、R5、R6和m的定义如本文所述。
• IMIDAZO- AND PYRROLO[1,2-A]PYRIMID-4-ONES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS
  申请人：Neurocrine Biosciences, Inc.

  公开号：EP1185530A1

  公开（公告）日：2002-03-13
• US8324209B2
  申请人：——

  公开号：US8324209B2

  公开（公告）日：2012-12-04
• [EN] IMIDAZO- AND PYRROLO[1,2-A]PYRIMID-4-ONES AS GONADOTROPIN-RELEASING HORMONE RECEPTOR ANTAGONISTS<br/>[FR] IMIDAZO- ET PYRROLO[1,2-A]PYRIMID-4-ONES UTILISES COMME ANTAGONISTES DU RECEPTEUR DE L'HORMONE DE LIBERATION DE LA GONADOTROPHINE
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2000069859A1

  公开（公告）日：2000-11-23

  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 structure (I) including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein Ar, B, R1, R2, R3a, R3b, R4, R5, R6 and m are as defined herein.