1-(3-Methoxy-5-(trifluoromethyl)phenyl)piperazine | 227958-85-2

• 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: 1-(3-Methoxy-5-(trifluoromethyl)phenyl)piperazine
• 英文别名: 1-[3-methoxy-5-(trifluoromethyl)phenyl]piperazine
• CAS: 227958-85-2
• 化学式: C₁₂H₁₅F₃N₂O
• 分子量: 260.259
• InChiKey: YAQJEDMWAXBJDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-Methoxy-5-(trifluoromethyl)phenyl)piperazine 、 三氟乙酸 、 N-(4,6-dimethylpyridin-2-yl)-1H-imidazole-1-carbothioamide 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 N-(4,6-dimethylpyridin-2-yl)-4-(3-methoxy-5-(trifluoromethyl)phenyl)piperazine-1-carbothioamide trifluoroacetate
  参考文献：
  名称：

  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth

  摘要：

  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.

  DOI：

  10.1021/jm401752p
• 作为产物：
  描述：

  3-甲氧基-5-三氟甲基苯硼酸 在 copper diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 1-(3-Methoxy-5-(trifluoromethyl)phenyl)piperazine
  参考文献：
  名称：

  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth

  摘要：

  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.

  DOI：

  10.1021/jm401752p

文献信息

• BENZIMIDAZOLONE DERIVATIVES HAVING MIXED SEROTONINE AND DOPAMINE RECEPTORS AFFINITY
  申请人：BOEHRINGER INGELHEIM ITALIA S.p.A.

  公开号：EP1218352A1

  公开（公告）日：2002-07-03
• NOVEL CCR2 RECEPTOR ANTAGONISTS, METHOD FOR PRODUCING THE SAME, AND USE THEREOF AS MEDICAMENTS
  申请人：Ebel Heiner

  公开号：US20130123241A1

  公开（公告）日：2013-05-16

  The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) of formula (I) wherein HET is a group selected from among formulas (IIa) (IIb) (IIc) (IId) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD and pain diseases.
• US6281218B1
  申请人：——

  公开号：US6281218B1

  公开（公告）日：2001-08-28
• US8877745B2
  申请人：——

  公开号：US8877745B2

  公开（公告）日：2014-11-04
• [EN] PIPERAZINE DERIVATIVES USEFUL AS HYPOGLYCEMIC AGENTS<br/>[FR] DERIVES DE PIPERAZINE POUVANT ETRE UTILISES COMME AGENTS HYPOGLYCEMIQUES
  申请人：SHAMAN PHARMACEUTICALS, INC.

  公开号：WO1999031096A1

  公开（公告）日：1999-06-24

  (EN) Piperazine derivatives useful as antihyperglycemic agents, pharmaceutical compositions comprising the piperazine derivatives and methods for their use are described. The piperazine derivatives are useful for the treatment of insulin-dependent diabetes mellitus (IDDM or Type I) and non-insulin dependent diabetes mellitus (NIDDM or Type II).(FR) L'invention concerne des dérivés de pipérazine présentant une grande utilité comme agents antihyperglycémiques. L'invention traite également de compositions pharmaceutiques comprenant des dérivés de pipérazine et des procédés d'utilisation de ces derniers. Les dérivés de pipérazine permettent de traiter le diabète sucré insulinodépendant (ou de type I) et le diabète sucré non insulinodépendant (ou de type II).