4-(2-chloro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester | 847971-81-7

• 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: 4-(2-chloro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: 4-(2-Chloro-4-trifluoromethylphenyl)piperazine-1-carboxylic acid tert-butyl ester；tert-butyl 4-[2-chloro-4-(trifluoromethyl)phenyl]piperazine-1-carboxylate
• CAS: 847971-81-7
• 化学式: C₁₆H₂₀ClF₃N₂O₂
• 分子量: 364.795
• InChiKey: BMSUIVADKSNOPL-UHFFFAOYSA-N

物化性质

• 沸点：
  406.7±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以46%的产率得到1-(2-chloro-4-(trifluoromethyl)phenyl)piperazine
  参考文献：
  名称：

  [EN] 1- (2-AMINO-BENZOL) -PIPERAZINE DERIVATIVES AS GLYCINE UPTAKE INHIBITORS FOR THE TREATMENT OF PSYCHOSES
  [FR] DERIVES DE 1-(2-AMINO-BENZOL)-PIPERAZINE EN TANT QU'INHIBITEURS DE L'ABSORPTION DU GLYCOCOLLE POUR TRAITER DES PSYCHOSES

  摘要：

  具有式（I）的化合物，其中取代基如权利要求1中所述，用于治疗精神病、疼痛、记忆和学习中的神经退行性功能障碍、精神分裂症、痴呆症以及认知过程受损的其他疾病，如注意力缺陷障碍或阿尔茨海默病。

  公开号：

  WO2005023260A1
• 作为产物：
  描述：

  3-氯-4-碘三氟甲苯 、 N-Boc-哌嗪 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三(邻甲基苯基)磷 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 以10%的产率得到4-(2-chloro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  [EN] 1- (2-AMINO-BENZOL) -PIPERAZINE DERIVATIVES AS GLYCINE UPTAKE INHIBITORS FOR THE TREATMENT OF PSYCHOSES
  [FR] DERIVES DE 1-(2-AMINO-BENZOL)-PIPERAZINE EN TANT QU'INHIBITEURS DE L'ABSORPTION DU GLYCOCOLLE POUR TRAITER DES PSYCHOSES

  摘要：

  具有式（I）的化合物，其中取代基如权利要求1中所述，用于治疗精神病、疼痛、记忆和学习中的神经退行性功能障碍、精神分裂症、痴呆症以及认知过程受损的其他疾病，如注意力缺陷障碍或阿尔茨海默病。

  公开号：

  WO2005023260A1

文献信息

• Benzoyl-piperazine derivatives
  申请人：Alberati-Giani Daniela

  公开号：US20050070539A1

  公开（公告）日：2005-03-31

  A compound of formula wherein the substituents are as described in the specification for the treatment of psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

  一种化合物，其化学式为（在说明书中所述的取代基），用于治疗精神病、疼痛、记忆和学习中的神经退行性功能障碍、精神分裂症、痴呆症以及其他认知过程受损的疾病，例如注意力缺陷障碍或阿尔茨海默病。
• BENZOYL-PIPERAZINE DERIVATIVES
  申请人：Alberati-Giani Daniela

  公开号：US20090192136A1

  公开（公告）日：2009-07-30

  A compound of formula wherein the substituents are as described in the specification for the treatment of psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

  一种化合物，其化学式为，其中取代基如规范中所述，用于治疗精神病、疼痛、记忆和学习中的神经退行性功能障碍、精神分裂症、痴呆症和其他认知过程受损的疾病，如注意力缺陷障碍或阿尔茨海默病。
• 4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-<i>N</i>-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth
  作者：Timothy L. Foley、Ganesha Rai、Adam Yasgar、Thomas Daniel、Heather L. Baker、Matias Attene-Ramos、Nicolas M. Kosa、William Leister、Michael D. Burkart、Ajit Jadhav、Anton Simeonov、David J. Maloney

  DOI：10.1021/jm401752p

  日期：2014.2.13

  4'-Phosphopantetheinyl transferases (PPTases) catalyze a post-translational modification essential to bacterial cell viability and virulence. We present the discovery and medicinal chemistry optimization of 2-pyridinyl-N-(4-aryl)-piperazine-1-carbothioamides, which exhibit submicromolar inhibition of bacterial Sfp-PPTase with no activity toward the human orthologue. Moreover, compounds within this class possess antibacterial activity in the absence of a rapid cytotoxic response in human cells. An advanced analogue of this series, ML267 (55), was found to attenuate production of an Sfp-PPTase-dependent metabolite when applied to Bacillus subtilis at sublethal doses. Additional testing revealed antibacterial activity against methicillin-resistant Staphylococcus aureus, and chemical genetic studies implicated efflux as a mechanism for resistance in Escherichia coli. Additionally, we highlight the in vitro absorption, distribution, metabolism; and excretion and in vivo pharmacokinetic profiles of compound 55 to further demonstrate the potential utility of this small-molecule inhibitor.
• Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((<i>S</i>)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia
  作者：Emmanuel Pinard、Alexander Alanine、Daniela Alberati、Markus Bender、Edilio Borroni、Patrick Bourdeaux、Virginie Brom、Serge Burner、Holger Fischer、Dominik Hainzl、Remy Halm、Nicole Hauser、Synese Jolidon、Judith Lengyel、Hans-Peter Marty、Thierry Meyer、Jean-Luc Moreau、Roland Mory、Robert Narquizian、Mathias Nettekoven、Roger D. Norcross、Bernd Puellmann、Philipp Schmid、Sebastien Schmitt、Henri Stalder、Roger Wermuth、Joseph G. Wettstein、Daniel Zimmerli

  DOI：10.1021/jm100210p

  日期：2010.6.24

  The GlyT1 transporter has emerged as a key novel target for the treatment of schizophrenia. Herein, we report on the optimization of the 2-alkoxy-5-methylsulfonebenzoylpiperazine class of GlyT1 inhibitors to improve hERG channel selectivity and brain penetration. This effort culminated in the discovery of compound 10a (RG1678), the first potent and selective GlyT1 inhibitor to have a beneficial effect in schizophrenic patients in a phase II clinical trial.
• 1-(2-AMINO-BENZOYL)-PIPERAZINE DERIVATIVES AS GLYCINE UPTAKE INHIBITORS FOR THE TREATMENT OF PSYCHOSES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1663232B1

  公开（公告）日：2007-10-03