1-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone | 150558-01-3

• 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-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone
• 英文别名: 1-[4-[4-(Trifluoromethyl)phenyl]piperazin-1-yl]ethanone
• CAS: 150558-01-3
• 化学式: C₁₃H₁₅F₃N₂O
• 分子量: 272.27
• InChiKey: ZZCSTWQZYRXDJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对氯三氟甲苯 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.75h， 生成 1-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of aryl piperazines with potential as antidiabetic agents via the stimulation of glucose uptake and inhibition of NADH:ubiquinone oxidoreductase

  摘要：

  The management of blood glucose levels and the avoidance of diabetic hyperglycemia are common objectives of many therapies in the treatment of diabetes. An aryl piperazine compound 3a (RTC1) has been described as a promoter of glucose uptake, in part through a cellular mechanism that involves inhibition of NADH:ubiquinone oxidoreductase. We report herein the synthesis of 41 derivatives of 3a (RTC1) and a systematic structure-activity-relationship study where a number of compounds were shown to effectively stimulate glucose uptake in vitro and inhibit NADH:ubiquinone oxidoreductase. The hit compound 3a (RTC1) remained the most efficacious with a 2.57 fold increase in glucose uptake compared to vehicle control and micromolar inhibition of NADH:ubiquinone oxidoreductase (IC50 = 27 mu M). In vitro DMPK and in vivo PK studies are also described, where results suggest that 3a (RTC1) would not be expected to provoke adverse drug-drug interactions, yet be readily metabolised, avoid rapid excretion, with a short half-life, and have good tissue distribution. The overall results indicate that aryl piperazines, and 3a (RTC1) in particular, have potential as effective agents for the treatment of diabetes. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112416

文献信息

• [EN] N-ACYL-N'-PHENYLPIPERAZINE DERIVATIVES AS SRBP MODULATORS FOR USE IN THE TREATMENT OF DIABETES AND OBESITY<br/>[FR] DÉRIVÉS DE N-ACYL-N'-PHÉNYLPIPÉRAZINE UTILISÉS COMME MODULATEURS DE LA SRBP DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DU DIABÈTE ET DE L'OBÉSITÉ
  申请人：NAT UNIVERSITY OF IRELAND MAYNOOTH

  公开号：WO2013060860A1

  公开（公告）日：2013-05-02

  The present invention relates to compounds having the general formula (I) as described herein; methods of preparing said compounds; and their use in treating Type 1 and/or Type 2 Diabetes Mellitus. The compounds were assayed for binding to serum retinol binding protein (sRBP) and for disruption of the sRBP:transthyretin (TTR) and sRBP:sRBP receptor interaction. The compounds were also assayed for their ability to induce glucose uptake into mouse muscle cells. Also described is a pharmaceutical composition comprising a compound according to the first aspect of the present invention, and use thereof in treating Type 1 and Type 2 Diabetes.

  本发明涉及具有如下所述的一般式（I）的化合物；制备该化合物的方法；以及它们在治疗1型和/或2型糖尿病中的应用。对这些化合物进行了与血清视黄醇结合蛋白（sRBP）的结合和对sRBP：甲状腺素转运蛋白（TTR）和sRBP：sRBP受体相互作用的破坏的测定。这些化合物还被检测其促进小鼠肌肉细胞中葡萄糖摄取的能力。还描述了包含根据本发明第一方面的化合物的药物组合物，以及其在治疗1型和2型糖尿病中的用途。
• 一种绿色的可见光催化的乙酰胺化合物的制备方法
  申请人：苏州大学

  公开号：CN113717071B

  公开（公告）日：2023-08-01

  本发明公开了一种绿色的可见光催化的乙酰胺化合物的制备方法，该方法以LED灯作为光源提供能量，经济易得的芳香胺、脂肪胺以及市场可购买的2,3‑丁二酮作为反应底物。与现有技术相比较，本发明方法具有以下优点：1)采用绿色、高效、节能、环境友好的可见光催化的反应模式；2)反应体系简单且底物范围广，无需添加金属催化剂和脱水剂；3)反应产率较高；4)反应条件温和；5)操作比较简单；6)原料廉价易得。
• Tie-2 Modulators and Methods of Use
  申请人：Bannen Canne Lynne

  公开号：US20070275952A1

  公开（公告）日：2007-11-29

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinases, particularly Tie-2. Methods of using the compounds and pharmaceutical compositions thereof to treat kinase-dependent diseases and conditions are also an aspect of the invention.

  本发明提供了用于调节蛋白激酶酶活性以调节细胞活动，如增殖、分化、程序性细胞死亡、迁移和化学侵袭的化合物。本发明的化合物抑制、调节和/或调节激酶，特别是Tie-2。使用这些化合物及其制药组合物治疗激酶依赖性疾病和病况的方法也是本发明的一个方面。
• Design and synthesis of N-acyl and dimeric N-Arylpiperazine derivatives as potential antileishmanial agents
  作者：Shabina B. Ansari、Sakshi Kamboj、Karthik Ramalingam、Rachana Meena、Jhajan Lal、Ruchir Kant、Sanjeev K. Shukla、Neena Goyal、Damodara N. Reddy

  DOI：10.1016/j.bioorg.2023.106593

  日期：2023.8

  parenteral treatment for longer periods and the emergence of drug resistance. To develop affordable and potent antileishmanial agents, a series of N-acyl and homodimeric aryl piperazines were synthesized with high purity, predicted druggable properties by in silico methods and investigated their antileishmanial activity. The in vitro biological activity of synthesized compounds against clinically validated

  目前的利什曼病治疗方案与多种不良反应、昂贵的、较长时间的肠胃外治疗以及耐药性的出现有关。为了开发负担得起且有效的抗利什曼病药物，合成了一系列高纯度的N-酰基和同二聚芳基哌嗪，通过计算机方法预测了药物特性并研究了它们的抗利什曼病活性。合成化合物对经临床验证的杜氏利什曼原虫寄生虫细胞内无鞭毛体和细胞外前鞭毛体形式的体外生物活性表明，8 种化合物在浓度低于 25 µM 时可抑制 50% 的无鞭毛体生长。半数最大抑菌浓度（IC 50) 和八种活性化合物4a、4d和4e的细胞毒性评估表明其具有 IC 50 2.0 – 9.1 µM 和选择性指数 10 – 42 的活性。发现化合物4d（IC 50 2.0 µM，SI = 42）是其中最好的与对照药物米替福新相比，药效高四倍，毒性低八倍。总的来说，结果表明化合物4d是有前途的主要候选药物，可进一步开发为抗利什曼病药物。
• SEPIAPTERIN REDUCTASE INHIBITORS
  申请人：QUARTET MEDICINE, INC.

  公开号：US20170096435A1

  公开（公告）日：2017-04-06

  Inhibitors of sepiapterin reductase and uses of sepiapterin reductase inhibitors in analgesia, treatment of acute and chronic pain, anti-inflammation, and immune cell regulation are disclosed.