ethyl 4-({[2-amino-5-(4-methylpiperazin-1-yl)phenyl]methyl}amino)-2-(4-pyridyl)-1,3-thiazole-5-carboxylate | 630411-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: ethyl 4-({[2-amino-5-(4-methylpiperazin-1-yl)phenyl]methyl}amino)-2-(4-pyridyl)-1,3-thiazole-5-carboxylate
• 英文别名: ethyl 4-([{2-amino-5-(4-methylpiperazinyl)phenyl}methyl]amino)-2-(4-pyridyl)-1,3-thiazole-5-carboxylate；Ethyl 4-[[2-amino-5-(4-methylpiperazin-1-yl)phenyl]methylamino]-2-pyridin-4-yl-1,3-thiazole-5-carboxylate
• CAS: 630411-38-0
• 化学式: C₂₃H₂₈N₆O₂S
• 分子量: 452.58
• InChiKey: YDFUCABVOFLUDU-UHFFFAOYSA-N

物化性质

• 沸点：
  689.3±65.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 4-({[2-amino-5-(4-methylpiperazin-1-yl)phenyl]methyl}amino)-2-(4-pyridyl)-1,3-thiazole-5-carboxylate 在 sodium hydride 、 N,N'-羰基二咪唑 、 水 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.0h， 生成 ethyl 4-[6-(4-methylpiperazin-1-yl)-2-oxo-1,4-dihydroquinazolin-3(4H)-yl]-2-(4-pyridyl)-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-oxo-1,3,4-trihydroquinazolinyl derivatives and methods of use

  摘要：

  选定的化合物对于治疗疾病，如细胞增殖或凋亡介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物，药物组合物以及预防和治疗涉及中风、癌症等疾病和其他疾病或病症的方法。该发明还涉及制备这些化合物的方法，以及在这些方法中有用的中间体。

  公开号：

  US20030229068A1
• 作为产物：
  描述：

  ethyl 2-(pyridin-4-yl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate 、 2-(aminomethyl)-4-(4-methylpiperazinyl)phenylamine 以 1,4-二氧六环 为溶剂， 以70%的产率得到ethyl 4-({[2-amino-5-(4-methylpiperazin-1-yl)phenyl]methyl}amino)-2-(4-pyridyl)-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of 3,4-dihydro-1H-quinazolin-2-one derivatives as potential CDK5 inhibitors

  摘要：

  Cyclin-dependent kinase 5 (CDK5) is a serine/threonine kinase that plays a critical role in the early development of the nervous system. Deregulation of CDK5 is believed to contribute to the abnormal phosphorylation of various cellular substrates associated with neurodegenerative disorders such as Alzheimer's disease, amyotrophic lateral sclerosis, and ischemic stroke. Acyclic urea 3 was identified as a potent CDK5 inhibitor and co-crystallographic data of urea 3/CDK2 enzyme were used to design a novel series of 3,4-dihydroquinazolin-2(1H)-ones as CDK5 inhibitors. In this investigation we present our synthetic studies toward this series of compounds and discuss their biological relevance as CDK5 inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.005

文献信息

• 2-OXO-1,3,4-TRIHYDROQUINAZOLINYL DERIVATIVES FOR THE TREATMENT OF CELL PROLIFERATION-RELATED DISORDERS
  申请人：AMGEN INC.

  公开号：EP1507776B1

  公开（公告）日：2007-02-28
• US7119111B2
  申请人：——

  公开号：US7119111B2

  公开（公告）日：2006-10-10
• [EN] 2-OXO-1,3,4-TRIHYDROQUINAZOLINYL DERIVATIVES FOR THE TREATMENT OF CELL PROLIFERATION-RELATED DISORDERS<br/>[FR] DERIVES 2-OXO-1,3,4-TRIHYDROQUINAZOLINYLE UTILISES DANS LE TRAITEMENT DE TROUBLES ASSOCIES A LA PROLIFERATION DE CELLULES
  申请人：AMGEN INC

  公开号：WO2003101985A1

  公开（公告）日：2003-12-11

  Compounds of formula (I) are effective for treatment of cell proliferation or apoptosis mediated diseases. The invention encompasses novel compounds and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving stroke, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.
• Structure–activity relationships of 3,4-dihydro-1H-quinazolin-2-one derivatives as potential CDK5 inhibitors
  作者：Robert M. Rzasa、Matthew R. Kaller、Gang Liu、Ella Magal、Thomas T. Nguyen、Timothy D. Osslund、David Powers、Vincent J. Santora、Vellarkad N. Viswanadhan、Hui-Ling Wang、Xiaoling Xiong、Wenge Zhong、Mark H. Norman

  DOI：10.1016/j.bmc.2007.07.005

  日期：2007.10

  Cyclin-dependent kinase 5 (CDK5) is a serine/threonine kinase that plays a critical role in the early development of the nervous system. Deregulation of CDK5 is believed to contribute to the abnormal phosphorylation of various cellular substrates associated with neurodegenerative disorders such as Alzheimer's disease, amyotrophic lateral sclerosis, and ischemic stroke. Acyclic urea 3 was identified as a potent CDK5 inhibitor and co-crystallographic data of urea 3/CDK2 enzyme were used to design a novel series of 3,4-dihydroquinazolin-2(1H)-ones as CDK5 inhibitors. In this investigation we present our synthetic studies toward this series of compounds and discuss their biological relevance as CDK5 inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• 2-oxo-1,3,4-trihydroquinazolinyl derivatives and methods of use
  申请人：——

  公开号：US20030229068A1

  公开（公告）日：2003-12-11

  Selected compounds are effective for treatment of diseases, such as cell proliferation or apoptosis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving stroke, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选定的化合物对于治疗疾病，如细胞增殖或凋亡介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物，药物组合物以及预防和治疗涉及中风、癌症等疾病和其他疾病或病症的方法。该发明还涉及制备这些化合物的方法，以及在这些方法中有用的中间体。