(E)-5-羟基-7h-吡啶并[2,3-b]氮杂革-8(9h)-酮 | 652976-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E)-5-羟基-7h-吡啶并[2,3-b]氮杂革-8(9h)-酮
• 英文名称: 6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepine-5,8-dione
• 英文别名: 7,9-dihydro-6H-pyrido[2,3-b]azepine-5,8-dione
• CAS: 652976-28-8
• 化学式: C₉H₈N₂O₂
• mdl: MFCD06656948
• 分子量: 176.175
• InChiKey: MMRNZOSYBOQWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-羟基-7h-吡啶并[2,3-b]氮杂革-8(9h)-酮 在 硫酸 、 sodium acetate 、 palladium diacetate 、 三乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、1.03 MPa 条件下， 反应 10.67h， 生成 (E)-3-(6-oxo-5,6,7,12-tetrahydropyrido[2',3':2,3]azepino[4,5-b]indol-11-yl)-N-phenylacrylamide
  参考文献：
  名称：

  9- and 11-substituted 4-azapaullones are potent and selective inhibitors of African trypanosoma

  摘要：

  Trypanosomes from the "brucei" complex are pathogenic parasites endemic in sub-Saharan Africa and causative agents of severe diseases in humans and livestock. In order to identify new antitrypanosomal chemotypes against African trypanosomes, 4-azapaullones carrying α,β-unsaturated carbonyl chains in 9- or 11-position were synthesized employing a procedure with a Heck reaction as key step. Among the so prepared compounds, 5a and 5e proved to be potent antiparasitic agents with antitrypanosomal activity in the submicromolar range.

  DOI：

  10.1016/j.ejmech.2014.06.020
• 作为产物：
  描述：

  2-氨基烟酸乙酯 在 水 、 sodium hydride 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 生成 (E)-5-羟基-7h-吡啶并[2,3-b]氮杂革-8(9h)-酮
  参考文献：
  名称：

  1-Azakenpaullone is a selective inhibitor of glycogen synthase kinase-3β

  摘要：

  Kenpaullone derivatives with a modified parent ring system were synthesized in order to develop kinase inhibitors with enhanced selectivity. Among the novel structures, 1-azakenpaullone was found to act as a selective GSK-3beta versus CDK1 inhibitor. The charge distribution within the 1-azakenpaullone molecule is discussed as a possible explanation for the enhanced GSK-3beta selectivity of 1-azakenpaullone compared to other paullone derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.062

文献信息

• Lactam compounds useful as protein kinase inhibitors
  申请人：Blackburn Christopher

  公开号：US20060100194A1

  公开（公告）日：2006-05-11

  The present invention provides novel compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.

  本发明提供了一种新型化合物，可用作蛋白激酶抑制剂。本发明还提供了包含本发明化合物的制药组合物以及使用该组合物治疗各种疾病的方法。
• LACTAM COMPOUNDS USEFUL AS PROTEIN KINASE INHIBITORS
  申请人：Blackburn Christopher

  公开号：US20120178739A1

  公开（公告）日：2012-07-12

  The present invention provides novel compounds useful as inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various diseases.

  本发明提供了一种新型化合物，可用作蛋白激酶抑制剂。本发明还提供了包含所述化合物的药物组合物，以及使用该组合物治疗各种疾病的方法。
• Evaluation and Comparison of 3D-QSAR CoMSIA Models for CDK1, CDK5, and GSK-3 Inhibition by Paullones
  作者：Conrad Kunick、Kathrin Lauenroth、Karen Wieking、Xu Xie、Christiane Schultz、Rick Gussio、Daniel Zaharevitz、Maryse Leost、Laurent Meijer、Alexander Weber、Flemming S. Jørgensen、Thomas Lemcke

  DOI：10.1021/jm0308904

  日期：2004.1.1

  With a view to the rational design of selective GSK-3beta inhibitors, 3D-QSAR CoMSIA models were developed for the inhibition of the three serine/threonine kinases CDK1/cyclin B, CDK5/p25, and GSK-3beta by compounds from the paullone inhibitor family. The models are based on the kinase inhibition data of 52 paullone entities, which were aligned by a docking routine into the ATP-binding cleft of a CDK1/cyclin B homology model. Variation of grid spacing and column filtering were used during the optimization of the models. The predictive ability of the models was shown by a leave-one-out cross-validation and the prediction of an independent set of test compounds, which were synthesized especially for this purpose. Besides paullones with the basic indolo [3,2-d] [1]benzazepine core, the test set comprised novel thieno [3',2':2,3]-azepino[4,5-b]indoles, pyrido[2',3':2,3]azepino[4,5-b]indoles, and a pyrido[3',2':4,5]pyrrolo[3,2-d] [1]benzazepine. The best statistical values for the CoMSIA were obtained for the CDK1-models (r(2) = 0.929 and q(2) = 0.699), which were clearly superior to the models for CDK5 (r(2) = 0.874 and q(2) = 0.652) and GSK-3 (r(2) = 0.871 and q(2) = 0.554).
• US7459448B2
  申请人：——

  公开号：US7459448B2

  公开（公告）日：2008-12-02
• US7935694B2
  申请人：——

  公开号：US7935694B2

  公开（公告）日：2011-05-03