1-[3-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(2-methoxy-5-methyl-phenyl)-urea | 717897-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(2-methoxy-5-methyl-phenyl)-urea
• 英文别名: 1-[3-(4-Amino-7-cyclopentylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methoxy-5-methylphenyl)urea
• CAS: 717897-51-3
• 化学式: C₂₇H₂₈N₆O₃
• 分子量: 484.558
• InChiKey: GYFAPMADUQCILZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone 、 2-甲氧基-5-甲基苯基异氰酸酯 生成 1-[3-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(2-methoxy-5-methyl-phenyl)-urea
  参考文献：
  名称：

  Discovery and synthesis of novel 4-aminopyrrolopyrimidine Tie-2 kinase inhibitors for the treatment of solid tumors

  摘要：

  The synthesis and biological evaluation of novel Tie-2 kinase inhibitors are presented. Based on the pyrrolopyrimidine chemotype, several new series are described, including the benzimidazole series by linking a benzimidazole to the C5-position of the 4-amino-pyrrolopyrimidine core and the ketophenyl series synthesized by incorporating a ketophenyl group to the C5-position. Medicinal chemistry efforts led to potent Tie-2 inhibitors. Compound 15, a ketophenyl pyrrolopyrimidine urea analog with improved physicochemical properties, demonstrated favorable in vitro attributes as well as dose responsive and robust oral tumor growth inhibition in animal models. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.012

文献信息

• PYRROLOPYRIMIDINE DERIVATIVES
  申请人：Pfizer Products Inc.

  公开号：EP1578751B1

  公开（公告）日：2011-06-15
• Discovery and synthesis of novel 4-aminopyrrolopyrimidine Tie-2 kinase inhibitors for the treatment of solid tumors
  作者：Joel T. Arcari、Jean S. Beebe、Martin A. Berliner、Vincent Bernardo、Merin Boehm、Gary V. Borzillo、Tracey Clark、Bruce D. Cohen、Richard D. Connell、Heather N. Frost、Deborah A. Gordon、William M. Hungerford、Shefali M. Kakar、Aaron Kanter、Nandell F. Keene、Elizabeth A. Knauth、Susan D. LaGreca、Yong Lu、Louis Martinez-Alsina、Matthew A. Marx、Joel Morris、Nandini C. Patel、Doug Savage、Cathy I. Soderstrom、Carl Thompson、George Tkalcevic、Norma J. Tom、Felix F. Vajdos、James J. Valentine、Patrick W. Vincent、Matthew D. Wessel、Jinshan M. Chen

  DOI：10.1016/j.bmcl.2013.03.012

  日期：2013.5

  The synthesis and biological evaluation of novel Tie-2 kinase inhibitors are presented. Based on the pyrrolopyrimidine chemotype, several new series are described, including the benzimidazole series by linking a benzimidazole to the C5-position of the 4-amino-pyrrolopyrimidine core and the ketophenyl series synthesized by incorporating a ketophenyl group to the C5-position. Medicinal chemistry efforts led to potent Tie-2 inhibitors. Compound 15, a ketophenyl pyrrolopyrimidine urea analog with improved physicochemical properties, demonstrated favorable in vitro attributes as well as dose responsive and robust oral tumor growth inhibition in animal models. (C) 2013 Elsevier Ltd. All rights reserved.