7-benzyl-4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6-one | 1365627-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-benzyl-4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6-one
• CAS: 1365627-74-2
• 化学式: C₁₃H₁₀ClN₃O
• 分子量: 259.695
• InChiKey: ZAEMAZZXWKDTSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-benzyl-4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6-one 、 碘甲烷 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以68%的产率得到
  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
• 作为产物：
  描述：

  7-苄基-4-氯-7H-吡咯并[2,3-D]嘧啶 在 potassium peroxymonosulfate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以56%的产率得到7-benzyl-4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6-one
  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

• AKT AND P70 S6 KINASE INHIBITORS
  申请人：Shepherd Timothy Alan

  公开号：US20100120801A1

  公开（公告）日：2010-05-13

  The present invention provides AKT and p70 S6 kinase inhibitors of the formula: The present invention also provides pharmaceutical compositions comprising compounds of Formula I, uses of compounds of Formula I and methods of using compounds of Formula I.

  本发明提供了式子为AKT和p70 S6激酶抑制剂的药物。本发明还提供了包含式子I化合物的药物组合物，式子I化合物的用途以及使用式子I化合物的方法。
• US8148387B2
  申请人：——

  公开号：US8148387B2

  公开（公告）日：2012-04-03
• 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.