2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole | 308143-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole
• 英文别名: 2-amino-4-(4-methoxyphenyl)-5-methyl-1H-pyrrole-3-carbonitrile
• CAS: 308143-11-5
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: UVLHYGROYYKVRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙氧基甲叉丙二酸二乙酯 、 2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole 以 乙醇 、 diphenyl ether-biphenyl eutectic 为溶剂， 反应 24.5h， 以63%的产率得到3-cyano-6-ethoxycarbonyl-2-(4-methoxyphenyl)-1-methyl-4H-pyrrolo[1,2-a]pyrimid-7-one
  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
• 作为产物：
  描述：

  2-溴-1-(4-甲氧苯基)丙酮 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium azide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、248.21 kPa 条件下， 生成 2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole
  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。
• 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
• US6346534B1
  申请人：——

  公开号：US6346534B1

  公开（公告）日：2002-02-12
• [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.
• 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.