ethyl 2-(pyridin-4-yl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate | 630409-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(pyridin-4-yl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate
• 英文别名: ethyl 2-(4-pyridyl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate；ethyl 2-(pyridin-4-yl)-4-(((trifluoromethyl)sulfonyl)oxy)thiazole-5-carboxylate；ethyl 2-(pyridin-4-yl)-4-(trifluoromethylsulfonyloxy)thiazole-5-carboxylate；Ethyl 2-pyridin-4-yl-4-(trifluoromethylsulfonyloxy)-1,3-thiazole-5-carboxylate
• CAS: 630409-69-7
• 化学式: C₁₂H₉F₃N₂O₅S₂
• 分子量: 382.341
• InChiKey: FPIDHDUKKYLUCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  502.6±60.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl 2-(pyridin-4-yl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以12%的产率得到ethyl 4-amino-2-(pyridin-4-yl)thiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of trisubstituted thiazoles as Cdc7 kinase inhibitors

  摘要：

  The Cell division cycle 7 (Cdc7) protein kinase is essential for DNA replication and maintenance of genome stability. We systematically explored thiazole-based compounds as inhibitors of Cdc7 kinase activity in cancer cells. Our studies resulted in the identification of a potent, selective Cdc7 inhibitor that decreased phosphorylation of the direct substrate MCM2 in vitro and in vivo, and inhibited DNA synthesis and cell viability in vitro.

  DOI：

  10.1016/j.ejmech.2014.04.013
• 作为产物：
  描述：

  硫代异烟酰胺 在 吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 ethyl 2-(pyridin-4-yl)-4-[(trifluoromethyl)sulfonyloxy]-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of trisubstituted thiazoles as Cdc7 kinase inhibitors

  摘要：

  The Cell division cycle 7 (Cdc7) protein kinase is essential for DNA replication and maintenance of genome stability. We systematically explored thiazole-based compounds as inhibitors of Cdc7 kinase activity in cancer cells. Our studies resulted in the identification of a potent, selective Cdc7 inhibitor that decreased phosphorylation of the direct substrate MCM2 in vitro and in vivo, and inhibited DNA synthesis and cell viability in vitro.

  DOI：

  10.1016/j.ejmech.2014.04.013

文献信息

• 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。
• 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.
• Thiazole–aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors
  作者：Variam Ullas Jeankumar、Janupally Renuka、Peddi Santosh、Vijay Soni、Jonnalagadda Padma Sridevi、Priyanka Suryadevara、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2013.09.025

  日期：2013.12

  A series of ethyl-4-(4-((substituted benzyl)amino)piperidin-1-yl)-2-(phenyl/pyridyl)thiazole-5-carboxy lates was designed by molecular hybridization and synthesized from aryl thioamides in five steps. The compounds were evaluated for their in vitro Mycobacterium smegmatis (MS) GyrB ATPase assay, Mycobacterium tuberculosis (MTB) DNA gyrase super coiling assay, antituberculosis activity and cytotoxicity. Among the twenty four compounds studied, ethyl-4-(44(4-fluorobenzypamino)piperidin-1-y1)-2-phenylthiazole-5-carboxylate (14) was found to be the promising compound which showed activity against all test with MS GyrB IC50 of 24.0 +/- 2.1 mu M, 79% inhibition of MTB DNA gyrase at 50 tM, MTB MIC of 28.44 mu M, and not cytotoxic at 50 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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