4-[(3R)-3-aminopyrrolidin-1-yl]-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine | 1417521-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[(3R)-3-aminopyrrolidin-1-yl]-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• CAS: 1417521-24-4
• 化学式: C₁₆H₁₇FN₆
• 分子量: 312.35
• InChiKey: PEQLQRNUKZZPNP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  96.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-amino-6-(4-fluorophenyl)-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one 、 (R)-3-叔丁氧羰基氨基吡咯烷 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[(3R)-3-aminopyrrolidin-1-yl]-6-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
  参考文献：
  名称：

  Synthesis and evaluation of novel ligands for the histamine H4 receptor based on a pyrrolo[2,3-d]pyrimidine scaffold

  摘要：

  Starting from a known H4R ligand based on a pyrimidine skeleton, a series of novel analogues based on a pyrrolo[2,3-d]pyrimidine scaffold have been prepared. Whereas the original pyrimidine congener shows good affinity at hH(4)R (K-i = 0.5 mu M), its lacks selectivity with a K-i value for the hH(3)R of 1 mu M. Within the newly synthesized pyrrolo[2,3-d]pyrimidines, several congeners show K-i values of less than 1 mu M at the hH(4)R and show a much improved selectivity profile. Therefore, these series represent an interesting starting point for the discovery of novel hH(4)R ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.139

文献信息

• Synthesis and evaluation of novel ligands for the histamine H4 receptor based on a pyrrolo[2,3-d]pyrimidine scaffold
  作者：Ling-Jie Gao、J. Stephan Schwed、Lilia Weizel、Steven De Jonghe、Holger Stark、Piet Herdewijn

  DOI：10.1016/j.bmcl.2012.10.139

  日期：2013.1

  Starting from a known H4R ligand based on a pyrimidine skeleton, a series of novel analogues based on a pyrrolo[2,3-d]pyrimidine scaffold have been prepared. Whereas the original pyrimidine congener shows good affinity at hH(4)R (K-i = 0.5 mu M), its lacks selectivity with a K-i value for the hH(3)R of 1 mu M. Within the newly synthesized pyrrolo[2,3-d]pyrimidines, several congeners show K-i values of less than 1 mu M at the hH(4)R and show a much improved selectivity profile. Therefore, these series represent an interesting starting point for the discovery of novel hH(4)R ligands. (C) 2012 Elsevier Ltd. All rights reserved.