ethyl 2-phenyl-4-(((trifluoromethyl)sulfonyl)oxy)thiazole-5-carboxylate | 351428-18-7

• 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-phenyl-4-(((trifluoromethyl)sulfonyl)oxy)thiazole-5-carboxylate
• 英文别名: ethyl 2-phenyl-4-[(trifluoromethanesulfonyl)oxy]-1,3-thiazole-5-carboxylate；2-phenyl-4-trifluoromethanesulfonyloxy-thiazole-5-carboxylic acid ethyl ester；ethyl 2-phenyl-4-(trifluoromethylsulfonyloxy)-1,3-thiazole-5-carboxylate
• CAS: 351428-18-7
• 化学式: C₁₃H₁₀F₃NO₅S₂
• 分子量: 381.353
• InChiKey: YXUIEGFECKTWMW-UHFFFAOYSA-N

物化性质

• 沸点：
  473.6±55.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2-phenyl-4-(((trifluoromethyl)sulfonyl)oxy)thiazole-5-carboxylate 在 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 ethyl 4-(4-((4-(benzyloxy)benzyl)amino)piperidin-1-yl)-2-phenylthiazole-5-carboxylate
  参考文献：
  名称：

  Thiazole–aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.09.025
• 作为产物：
  描述：

  硫代苯甲酰胺 在 吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 ethyl 2-phenyl-4-(((trifluoromethyl)sulfonyl)oxy)thiazole-5-carboxylate
  参考文献：
  名称：

  Thiazole–aminopiperidine hybrid analogues: Design and synthesis of novel Mycobacterium tuberculosis GyrB inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.09.025

文献信息

• Gyrase inhibitors and uses thereof
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US06608087B1

  公开（公告）日：2003-08-19

  The present invention relates to compounds of the formula I: where Ring A is a thiazole, oxazole, imidazole or pyrazole and the substituents are as described in the specification, and pharmaceutically acceptable salts thereof. The compounds inhibit bacterial gyrase activity and therefore are useful for treating bacterial infections in mammals.

  本发明涉及式I化合物： 其中，环A是噻唑、恶唑、咪唑或吡唑，取代基如说明书中所述，以及药用可接受的盐。这些化合物抑制细菌旋转酶活性，因此可用于治疗哺乳动物的细菌感染。
• Trpm8 antagonists
  申请人：Dompe' S.P.A.

  公开号：EP2606888A1

  公开（公告）日：2013-06-26

  The invention relates to compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRPM8), and having formula: Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, inflammatory conditions and urological disorders.

  该发明涉及作为瞬时受体电位阳离子通道亚家族M成员8（TRPM8）的选择性拮抗剂的化合物，其化学式为：这些化合物在治疗与TRPM8活性相关的疾病方面具有用途，如疼痛、炎症、缺血、神经退行性疾病、中风、精神障碍、炎症性疾病和泌尿系统疾病。
• [EN] TRPM8 ANTAGONISTS<br/>[FR] ANTAGONISTES DE TRPM8
  申请人：DOMPE SPA

  公开号：WO2013092711A1

  公开（公告）日：2013-06-27

  The invention relates to compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRPM8), and having formula (I). Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, itch, irritable bowel diseases, cold induced and/or exhacerbated respiratory disorders and urological disorders.

  该发明涉及作为Transient Receptor Potential阳离子通道亚家族M成员8 (TRPM8)的选择性拮抗剂的化合物，其化学式为(I)。所述化合物在治疗与TRPM8活性相关的疾病方面具有用途，如疼痛、炎症、缺血、神经退行性疾病、中风、精神障碍、瘙痒、肠易激综合征、冷诱导和/或加重的呼吸道疾病以及泌尿系统疾病。
• Discovery of Novel TRPM8 Blockers Suitable for the Treatment of Somatic and Ocular Painful Conditions: A Journey through p<i>K</i>_a and LogD Modulation
  作者：Gianluca Bianchini、Mara Tomassetti、Samuele Lillini、Anna Sirico、Silvia Bovolenta、Lorena Za、Chiara Liberati、Rubina Novelli、Andrea Aramini

  DOI：10.1021/acs.jmedchem.1c01647

  日期：2021.11.25
• Discovery of pyrazolthiazoles as novel and potent inhibitors of bacterial gyrase
  作者：Steven M. Ronkin、Michael Badia、Steve Bellon、Anne-Laure Grillot、Christian H. Gross、Trudy H. Grossman、Nagraj Mani、Jonathan D. Parsons、Dean Stamos、Martin Trudeau、Yunyi Wei、Paul S. Charifson

  DOI：10.1016/j.bmcl.2010.03.052

  日期：2010.5

  Bacterial DNA gyrase is an attractive target for the investigation of new antibacterial agents. Inhibitors of the GyrB subunit, which contains the ATP-binding site, are described in this communication. Novel, substituted 5-(1H-pyrazol-3-yl)thiazole compounds were identified as inhibitors of bacterial gyrase. Structure-guided optimization led to greater enzymatic potency and moderate antibacterial potency. Data are presented for the demonstration of selective enzyme inhibition of Escherichia coli GyrB over Staphylococcus aureus GyrB.