4-[[4-[7-[[2-(Trifluoromethyl)phenyl]methyl]pyrrolo[2,3-d]pyrimidin-4-yl]oxypiperidin-1-yl]methyl]-1,3-thiazole | 1365626-80-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[[4-[7-[[2-(Trifluoromethyl)phenyl]methyl]pyrrolo[2,3-d]pyrimidin-4-yl]oxypiperidin-1-yl]methyl]-1,3-thiazole
• CAS: 1365626-80-7
• 化学式: C₂₃H₂₂F₃N₅OS
• 分子量: 473.522
• InChiKey: UMLBPTKZCLVUIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-氯吡咯并嘧啶 在 sodium hydride 、 potassium carbonate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 16.0h， 生成 4-[[4-[7-[[2-(Trifluoromethyl)phenyl]methyl]pyrrolo[2,3-d]pyrimidin-4-yl]oxypiperidin-1-yl]methyl]-1,3-thiazole
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of pyrrolopyrimidines as potent, state-dependent Nav1.7 antagonists

  摘要：

  Herein we describe the discovery, optimization, and structure-activity relationships of novel potent pyrrolopyrimidine Na(v)1.7 antagonists. Hit-to-lead SAR studies of the pyrrolopyrimidine core, head, and tail groups of the molecule led to the identification of pyrrolopyrimidine 48 as exceptionally potent Na(v)1.7 blocker with good selectivity over hERG and improved microsomal stability relative to our hit molecule and pyrazolopyrimidine 8 as a promising starting point for future optimization efforts. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.01.015

文献信息

• Discovery and hit-to-lead optimization of pyrrolopyrimidines as potent, state-dependent Nav1.7 antagonists
  作者：Nagasree Chakka、Howie Bregman、Bingfan Du、Hanh Nho Nguyen、John L. Buchanan、Elma Feric、Joseph Ligutti、Dong Liu、Jeff S. McDermott、Anruo Zou、Stefan I. McDonough、Erin F. DiMauro

  DOI：10.1016/j.bmcl.2012.01.015

  日期：2012.3

  Herein we describe the discovery, optimization, and structure-activity relationships of novel potent pyrrolopyrimidine Na(v)1.7 antagonists. Hit-to-lead SAR studies of the pyrrolopyrimidine core, head, and tail groups of the molecule led to the identification of pyrrolopyrimidine 48 as exceptionally potent Na(v)1.7 blocker with good selectivity over hERG and improved microsomal stability relative to our hit molecule and pyrazolopyrimidine 8 as a promising starting point for future optimization efforts. Published by Elsevier Ltd.