1,2-bis[3-(2-diethylaminoethoxy)phenyl]ethane-1,2-dione | 58931-32-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis[3-(2-diethylaminoethoxy)phenyl]ethane-1,2-dione
• 英文别名: 3,3'-Bis(2-Diethylaminoethoxy)Benzil；1,2-Bis[3-[2-(diethylamino)ethoxy]phenyl]ethane-1,2-dione
• CAS: 58931-32-1
• 化学式: C₂₆H₃₆N₂O₄
• 分子量: 440.583
• InChiKey: QQAFZYYYKGVJAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4,5,6-四氨基嘧啶 、 1,2-bis[3-(2-diethylaminoethoxy)phenyl]ethane-1,2-dione 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 10.0h， 生成 6,7-Bis({3-[2-(diethylamino)ethoxy]phenyl})pteridine-2,4-diamine
  参考文献：
  名称：

  Discovery of 3,3‘-(2,4-Diaminopteridine-6,7-diyl)diphenol as an Isozyme-Selective Inhibitor of PI3K for the Treatment of Ischemia Reperfusion Injury Associated with Myocardial Infarction

  摘要：

  In studies aimed toward identifying effective and safe inhibitors of kinase signaling cascades that underlie ischemia/reperfusion (I/R) injury, we synthesized a series of pteridines and pyridopyrazines. The design strategy was inspired by the examination of naturally occurring PI3K inhibitors such as wortmannin and quercetin, and building a pharmacophore-based model used for optimization. Structural modifications led to hybrid molecules which incorporated aminopyrimidine and aminopyridine moieties with ATP mimetic characteristics into the pharmacophore motifs to modulate kinase affinity and selectivity. Elaborations involving substitutions of the 2 and 4 positions of the pyrimidine or pyridine ring and the 6 and 7 positions of the central pyrazine ring resulted in in vivo activity profiles which identified potent inhibitors of vascular endothelial growth factor (VEGF) induced vascular leakage. Pathway analysis identified a diaminopteridine-diphenol as a potent and selective phosphatidylinositol-3-kinase (PI3K) inhibitor. The structure -activity relationship studies of various analogues of diaminopteridine-diphenol-based on biochemical assays resulted in potent inhibitors of PI3K.

  DOI：

  10.1021/jm051056c
• 作为产物：
  描述：

  3,3'-dihydroxybenzil dithallium salt 、 N,N-二乙基氯乙胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 1,2-bis[3-(2-diethylaminoethoxy)phenyl]ethane-1,2-dione
  参考文献：
  名称：

  Aminoalkyl ethers of 2,2'- and 3,3'-dihydroxybenzil

  摘要：

  通过将2,2'-或3,3'-二羟基苯并咪唑的二铊盐与二烷基氨基烷氯化物反应制备了2,2'-和3,3'-二羟基苯并咪唑的二烷基氨基烷醚。这些产物具有抗心律失常活性。

  公开号：

  US03935191A1

文献信息

• US3935191A
  申请人：——

  公开号：US3935191A

  公开（公告）日：1976-01-27
• US3962334A
  申请人：——

  公开号：US3962334A

  公开（公告）日：1976-06-08
• Aminoalkyl ethers of 2,2'- and 3,3'-dihydroxybenzil
  申请人：American Home Products Corporation

  公开号：US03935191A1

  公开（公告）日：1976-01-27

  Dialkylaminoalkyl ethers of 2,2'- and 3,3'-dihydroxybenzil are prepared by reacting the dithallium salt of 2,2'- or 3,3'-dihydroxybenzil with a dialkylaminoalkylchlorde. The products have antiarrhythmic activity.

  通过将2,2'-或3,3'-二羟基苯并咪唑的二铊盐与二烷基氨基烷氯化物反应制备了2,2'-和3,3'-二羟基苯并咪唑的二烷基氨基烷醚。这些产物具有抗心律失常活性。
• Discovery of 3,3‘-(2,4-Diaminopteridine-6,7-diyl)diphenol as an Isozyme-Selective Inhibitor of PI3K for the Treatment of Ischemia Reperfusion Injury Associated with Myocardial Infarction
  作者：Moorthy S. S. Palanki、Elena Dneprovskaia、John Doukas、Richard M. Fine、John Hood、Xinshan Kang、Dan Lohse、Michael Martin、Glenn Noronha、Richard M. Soll、Wolfgang Wrasidlo、Shiyin Yee、Hong Zhu

  DOI：10.1021/jm051056c

  日期：2007.9.1

  In studies aimed toward identifying effective and safe inhibitors of kinase signaling cascades that underlie ischemia/reperfusion (I/R) injury, we synthesized a series of pteridines and pyridopyrazines. The design strategy was inspired by the examination of naturally occurring PI3K inhibitors such as wortmannin and quercetin, and building a pharmacophore-based model used for optimization. Structural modifications led to hybrid molecules which incorporated aminopyrimidine and aminopyridine moieties with ATP mimetic characteristics into the pharmacophore motifs to modulate kinase affinity and selectivity. Elaborations involving substitutions of the 2 and 4 positions of the pyrimidine or pyridine ring and the 6 and 7 positions of the central pyrazine ring resulted in in vivo activity profiles which identified potent inhibitors of vascular endothelial growth factor (VEGF) induced vascular leakage. Pathway analysis identified a diaminopteridine-diphenol as a potent and selective phosphatidylinositol-3-kinase (PI3K) inhibitor. The structure -activity relationship studies of various analogues of diaminopteridine-diphenol-based on biochemical assays resulted in potent inhibitors of PI3K.