(S)-4-(2-chloro-7-methyl-7H-purin-6-yl)-3-ethylmorpholine | 1285500-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (S)-4-(2-chloro-7-methyl-7H-purin-6-yl)-3-ethylmorpholine
• 英文别名: (3S)-4-(2-chloro-7-methylpurin-6-yl)-3-ethylmorpholine
• CAS: 1285500-26-6
• 化学式: C₁₂H₁₆ClN₅O
• 分子量: 281.745
• InChiKey: JJTIGCKUMLWXKD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-乙基脲)苯硼酸频哪酯 、 (S)-4-(2-chloro-7-methyl-7H-purin-6-yl)-3-ethylmorpholine 在 四(三苯基膦)钯 、 potassium acetate 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 (S)-1-ethyl-3-(4-(6-(3-ethylmorpholino)-7-methyl-7H-purin-2-yl)phenyl)urea
  参考文献：
  名称：

  A hit to lead discovery of novel N-methylated imidazolo-, pyrrolo-, and pyrazolo-pyrimidines as potent and selective mTOR inhibitors

  摘要：

  A series of N-7-methyl-imidazolopyrimidine inhibitors of the mTOR kinase have been designed and prepared, based on the hypothesis that the N-7-methyl substituent on imidazolopyrimidine would impart selectivity for mTOR over the related PI3K alpha and delta kinases. The corresponding N-Me substituted pyrrolo[3,2-d]pyrimidines and pyrazolo[4,3-d]pyrimidines also show potent mTOR inhibition with selectivity toward both PI3 alpha and delta kinases. The most potent compound synthesized is pyrazolo[4,3-d]pyrimidine 21c. Compound 21c shows a K-i of 2 nM against mTOR inhibition, remarkable selectivity (>2900x) over PI3 kinases, and excellent potency in cell-based assays. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.027
• 作为产物：
  描述：

  可可碱 在 N,N-二异丙基乙胺 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (S)-4-(2-chloro-7-methyl-7H-purin-6-yl)-3-ethylmorpholine
  参考文献：
  名称：

  A hit to lead discovery of novel N-methylated imidazolo-, pyrrolo-, and pyrazolo-pyrimidines as potent and selective mTOR inhibitors

  摘要：

  A series of N-7-methyl-imidazolopyrimidine inhibitors of the mTOR kinase have been designed and prepared, based on the hypothesis that the N-7-methyl substituent on imidazolopyrimidine would impart selectivity for mTOR over the related PI3K alpha and delta kinases. The corresponding N-Me substituted pyrrolo[3,2-d]pyrimidines and pyrazolo[4,3-d]pyrimidines also show potent mTOR inhibition with selectivity toward both PI3 alpha and delta kinases. The most potent compound synthesized is pyrazolo[4,3-d]pyrimidine 21c. Compound 21c shows a K-i of 2 nM against mTOR inhibition, remarkable selectivity (>2900x) over PI3 kinases, and excellent potency in cell-based assays. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.027

文献信息

• N-7 SUBSTITUTED PURINE AND PYRAZOLOPYRIMINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Pei Zhonghua

  公开号：US20110086840A1

  公开（公告）日：2011-04-14

  The present invention relates to compounds of Formula I: wherein R 1 , R 2 , R 3 , A 1 , A 2 , A 3 , A 4 , Y 1 and Y 2 and D have the meaning described herein. The present invention also relates to pharmaceutical compositions comprising such compounds and therapeutic uses thereof.

  本发明涉及以下式I的化合物： 其中R1、R2、R3、A1、A2、A3、A4、Y1和Y2以及D具有本文所描述的含义。本发明还涉及包含此类化合物的药物组合物以及其治疗用途。
• N-7 substituted purine and pyrazolopyrimine compounds, compositions and methods of use
  申请人：Pei Zhonghua

  公开号：US08828990B2

  公开（公告）日：2014-09-09

  The present invention relates to compounds of Formula I: wherein R1, R2, R3, A1, A2, A3, A4, Y1 and Y2 and D have the meaning described herein. The present invention also relates to pharmaceutical compositions comprising such compounds and therapeutic uses thereof.

  本发明涉及式I的化合物：其中R1，R2，R3，A1，A2，A3，A4，Y1和Y2以及D具有本文所述的含义。本发明还涉及包含这种化合物的制药组合物和其治疗用途。
• N-7 SUBSTITUTED PURINE AND PYRAZOLOPYRIMIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2499143A1

  公开（公告）日：2012-09-19
• EP2499143B1
  申请人：——

  公开号：EP2499143B1

  公开（公告）日：2016-03-16
• US8828990B2
  申请人：——

  公开号：US8828990B2

  公开（公告）日：2014-09-09