3-cyano-6-(3-pentyloxycarbonyl)-4-(2-fluorobenzyl)-2-(4-methoxyphenyl)-1-{N-methyl-N-[2-(2-pyridyl)ethyl]amino}methylpyrrolo[1,2-a]pyrimid-7-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-cyano-6-(3-pentyloxycarbonyl)-4-(2-fluorobenzyl)-2-(4-methoxyphenyl)-1-{N-methyl-N-[2-(2-pyridyl)ethyl]amino}methylpyrrolo[1,2-a]pyrimid-7-one
• 英文别名: 8-Cyano-1-(2-fluoro-benzyl)-7-(4-methoxy-phenyl)-6-{[methyl-(2-pyridin-2-yl-ethyl)-amino]-methyl}-4-oxo-1,4-dihydro-pyrrolo[1,2-a]pyrimidine-3-carboxylic acid 1-ethyl-propyl ester；pentan-3-yl 8-cyano-1-[(2-fluorophenyl)methyl]-7-(4-methoxyphenyl)-6-[[methyl(2-pyridin-2-ylethyl)amino]methyl]-4-oxopyrrolo[1,2-a]pyrimidine-3-carboxylate
• 化学式: C₃₇H₃₈FN₅O₄
• 分子量: 635.738
• InChiKey: YBCJKXKWUVGLAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氟溴苄 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙腈 为溶剂， 生成 3-cyano-6-(3-pentyloxycarbonyl)-4-(2-fluorobenzyl)-2-(4-methoxyphenyl)-1-{N-methyl-N-[2-(2-pyridyl)ethyl]amino}methylpyrrolo[1,2-a]pyrimid-7-one
  参考文献：
  名称：

  Initial Structure–Activity Relationship Studies of a Novel Series of Pyrrolo[1,2-a]pyrimid-7-ones as GnRH Receptor Antagonists

  摘要：

  Initial SAR studies on 1-aminomethyl-2-aryl-3-cyano-pyrrolo[1,2-a]pyrimid-7-one-6-carboxylates as human GnRH receptor antagonists were discussed. 2-(2-Methylaminoethyl)pyridine was discovered to be a key feature for generating active compounds. The best compound from the series had 25 nM (K-i) binding affinity to human GnRH receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00779-x

文献信息

• 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。
• Initial Structure–Activity Relationship Studies of a Novel Series of Pyrrolo[1,2-a]pyrimid-7-ones as GnRH Receptor Antagonists
  作者：Yun-Fei Zhu、R.Scott Struthers、Patrick J. Connors, Jr.、Yinghong Gao、Timothy D. Gross、John Saunders、Keith Wilcoxen、Greg J. Reinhart、Nicholas Ling、Chen Chen

  DOI：10.1016/s0960-894x(01)00779-x

  日期：2002.2

  Initial SAR studies on 1-aminomethyl-2-aryl-3-cyano-pyrrolo[1,2-a]pyrimid-7-one-6-carboxylates as human GnRH receptor antagonists were discussed. 2-(2-Methylaminoethyl)pyridine was discovered to be a key feature for generating active compounds. The best compound from the series had 25 nM (K-i) binding affinity to human GnRH receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.