4-fluoro-N-(piperidine-1-carbonothioyl)benzamide | 446308-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-N-(piperidine-1-carbonothioyl)benzamide
• 英文别名: N-(piperidinylthiocarbonyl)-4-fluorobenzamide；4-fluoro-N-(piperidine-1-carbothioyl)benzamide
• CAS: 446308-66-3
• 化学式: C₁₃H₁₅FN₂OS
• 分子量: 266.339
• InChiKey: PKVKIVMZLTVTOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 4-fluoro-N-(piperidine-1-carbonothioyl)benzamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 以74%的产率得到[Cu(N-4-fluorobenzoylpiperidine-1-carbothioimidate)₂]
  参考文献：
  名称：

  Crystal structures and antimicrobial activities of copper(II) complexes of fluorine-containing thioureido ligands

  摘要：

  Cu(II) complexes with N-4-fluorobenzoylpiperidine-1-carbothioimidate (L1(-)), N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2(-)) and 2-fluorobenzoate (L3(-)) have been synthesized and characterized by elemental analysis, Fourier Transform infrared (FT-IR), Ultraviolet (UV) and fluorescence spectroscopy methods. The crystal structures of [Cu(L1)(2)], [Cu(L2)(2)] and [Cu-2(L3)(4)(DMF)(2)] (DMF: N,N-dimethylformamide) have been determined by X-ray diffraction method. The antimicrobial activities of the complexes against the bacteria (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Shewanella sp.) and the fungi (Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp.) have been investigated comparing with the corresponding ligands. The experiments showed that the complexes had the stronger antibacterial and antifungal activities than the corresponding ligands had. (C) 2013 The Authors. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.06.029
• 作为产物：
  描述：

  对氟苯甲酸 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 4-fluoro-N-(piperidine-1-carbonothioyl)benzamide
  参考文献：
  名称：

  Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)

  摘要：

  合成了 N-2-氟苯甲酰基哌啶-1-硫代亚胺酸（L2-）、N-4-氟苯甲酰基哌啶-1-硫代亚胺酸（L3-）、N-2-氟苯甲酰基吗啉-1-硫代亚胺酸（L5-）和 N-4-氟苯甲酰基吗啉-1-硫代亚胺酸（L6-）的 Ni(II) 配合物，并通过元素分析、傅立叶变换红外光谱和 1H-NMR 对其进行了表征。 通过 X 射线衍射测定了三种配体（HL2、HL3 和 HL6）和相应的 Ni(II) 复合物（[Ni(L2)2]、[Ni(L3)2] 和 [Ni(L6)2]）的晶体结构。研究了 Ni(II) 复合物和相应配体对灰霉病菌、毛霉属真菌、霉菌和轮枝霉菌的抗真菌活性。实验结果表明，配体及其配合物具有抗真菌能力。当对苯甲酰基上的氟被取代后，配体的抗真菌活性明显提高。此外，配体对真菌的抑制作用强于其配合物。HL6 的抗真菌能力特别强，与商用杀真菌剂氟康唑的抗真菌能力相似。

  DOI：

  10.3390/molecules181215737

文献信息

• Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase
  作者：Shweta Sinha、Mukesh Doble、S.L. Manju

  DOI：10.1016/j.ejmech.2018.08.098

  日期：2018.10

  only drug against 5-LOX, was withdrawn from the market due to several problems. In the present study, the performance of rationally designed conjugates of thiazole (2) and thiourea (3) scaffolds from our previously reported 2-amino-4-aryl thiazole (1) is reported. They are synthesized (total 31 derivatives), characterized, and tested against the 5-LOX enzyme in vitro and the mode of action of the most

  人5-脂氧合酶（5-LOX）是针对哮喘和炎症的关键酶。Zileuton是唯一一种针对5-LOX的药物，由于几个问题而退出市场。在本研究中，报道了我们先前报道的2-氨基-4-芳基噻唑（1）对噻唑（2）和硫脲（3）支架进行合理设计的偶联物的性能。它们是合成的（总共31个衍生物），在体外进行了表征并针对5-LOX酶进行了测试，并确定了活性最高的酶的作用方式。化合物2m的IC 500.9±0.1μM的化合物通过竞争性（非氧化还原）机理起作用，与Zileuton不同，它没有自由基清除性能。计算研究与支持其作用机理的实验数据非常吻合。来自硫脲系列（3）的另一个铅分子3f对5-LOX的IC 50为1.4±0.1μM，其作用方式为氧化还原类型（非竞争性）。有希望地注意到，铅抑制剂2m和3f表现出的活性均优于商品药物Zileuton（IC 50  = 1.5  ±  0.3μM）。这些抑制剂可以进一步发展为抗炎药。
• Synthesis, structures and antibacterial activities of benzoylthiourea derivatives and their complexes with cobalt
  作者：Wen Yang、Huanhuan Liu、Mengying Li、Fan Wang、Weiqun Zhou、Jianfen Fan

  DOI：10.1016/j.jinorgbio.2012.08.001

  日期：2012.11

  Four new thiocarbonyl fluorobenzamides and their complexes with cobalt have been synthesized and characterized by elemental analysis, FTIR, and H-1 NMR. Five crystal structures of the thioylbenzamides complexes of Co(PTCB)(3), Co(2FPTCB)(3), Co(4FPTCB)(3), Co(2FMTCB)(2) and Co(4FMTCB)(3) have been determined by X-ray diffraction. The antibacterial properties of these compounds against the bacteria, E. coli, Staphylococcus aureus, B. subtilis, P. aeruginosa, and Shewanella sp. were investigated. The experiments showed that both compounds and the complexes had the antibacterial activities against all of the studied bacteria. The thioylbenzamides had stronger controls for the bacteria of E. coli, S. aureus, B. subtilis and P. aeruginosa than their corresponding cobalt complexes. There was the contrary result against the bacteria of Shewanella sp. The para-substitution of fluorine atom increased antibacterial activities, while fluorine atom was substituted on ortho-benzoyl, the antibacterial activity weakened. The thioylbenzamides linked to piperidine instead of a morpholine group may increase the antibacterial activities. (c) 2012 Elsevier Inc. All rights reserved.
• Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)
  作者：Chun Li、Wen Yang、Huanhuan Liu、Mengying Li、Weiqun Zhou、Juan Xie

  DOI：10.3390/molecules181215737

  日期：——

  Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2−), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3−), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5−) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6−) have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3 and HL6) and the corresponding Ni(II) complexes ([Ni(L2)2], [Ni(L3)2] and [Ni(L6)2]) have been determined by X-ray diffraction. The antifungal activities of the Ni(II) complexes together and the corresponding ligands against the fungi Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp. have been investigated. The experimental results showed that the ligands and their complexes have antifungal abilities. When the fluorine was substituted on the para-benzoyl moiety, the antifungal activity of the ligands was obviously increased. Moreover, the ligands were stronger than their complexes in inhibiting fungal activities. The antifungal ability of HL6 is especially strong, and similar to that of the commercial fungicide fluconazole.

  合成了 N-2-氟苯甲酰基哌啶-1-硫代亚胺酸（L2-）、N-4-氟苯甲酰基哌啶-1-硫代亚胺酸（L3-）、N-2-氟苯甲酰基吗啉-1-硫代亚胺酸（L5-）和 N-4-氟苯甲酰基吗啉-1-硫代亚胺酸（L6-）的 Ni(II) 配合物，并通过元素分析、傅立叶变换红外光谱和 1H-NMR 对其进行了表征。 通过 X 射线衍射测定了三种配体（HL2、HL3 和 HL6）和相应的 Ni(II) 复合物（[Ni(L2)2]、[Ni(L3)2] 和 [Ni(L6)2]）的晶体结构。研究了 Ni(II) 复合物和相应配体对灰霉病菌、毛霉属真菌、霉菌和轮枝霉菌的抗真菌活性。实验结果表明，配体及其配合物具有抗真菌能力。当对苯甲酰基上的氟被取代后，配体的抗真菌活性明显提高。此外，配体对真菌的抑制作用强于其配合物。HL6 的抗真菌能力特别强，与商用杀真菌剂氟康唑的抗真菌能力相似。
• Crystal structures and antimicrobial activities of copper(II) complexes of fluorine-containing thioureido ligands
  作者：Huanhuan Liu、Wen Yang、Weiqun Zhou、Yunlong Xu、Juan Xie、Mengying Li

  DOI：10.1016/j.ica.2013.06.029

  日期：2013.8

  Cu(II) complexes with N-4-fluorobenzoylpiperidine-1-carbothioimidate (L1(-)), N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2(-)) and 2-fluorobenzoate (L3(-)) have been synthesized and characterized by elemental analysis, Fourier Transform infrared (FT-IR), Ultraviolet (UV) and fluorescence spectroscopy methods. The crystal structures of [Cu(L1)(2)], [Cu(L2)(2)] and [Cu-2(L3)(4)(DMF)(2)] (DMF: N,N-dimethylformamide) have been determined by X-ray diffraction method. The antimicrobial activities of the complexes against the bacteria (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Shewanella sp.) and the fungi (Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp.) have been investigated comparing with the corresponding ligands. The experiments showed that the complexes had the stronger antibacterial and antifungal activities than the corresponding ligands had. (C) 2013 The Authors. Published by Elsevier B.V. All rights reserved.