1-thiocarbamoyl-5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole | 1072069-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-thiocarbamoyl-5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 5-(4-Fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide；3-(4-fluorophenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 1072069-72-7
• 化学式: C₁₆H₁₄FN₃S
• 分子量: 299.372
• InChiKey: ZAWNJNXLSZLLKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  235-237 °C
• 沸点：
  448.2±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-thiocarbamoyl-5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(4-fluorobenzylidene)-2-[5-(4-fluorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl]thiazol-4-one
  参考文献：
  名称：

  新型吡唑基噻唑类化合物作为潜在抗乳腺癌药物的合成及构效关系研究

  摘要：

  由5-（4-氟苯基）-3-芳基-4,5-二氢吡唑-1-碳硫酰胺衍生物与不同的试剂反应合成了一系列新的吡唑基噻唑。在光谱信息和元素分析的基础上，确保了所有新颖产品的机理和结构。估计了所有合成化合物相对于MCF-7细胞系的抗肿瘤活性。结果表明，一些测试样品显示出对人乳腺癌细胞系的强大活性。此外，还讨论了结构与活动之间的关系。

  DOI：

  10.1002/jhet.2794
• 作为产物：
  描述：

  对氟苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1-thiocarbamoyl-5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Novel pyrazoline linked acyl thiourea pharmacophores as antimicrobial, urease, amylase and α-glucosidase inhibitors: design, synthesis, SAR and molecular docking studies

  摘要：

  新合成的吡唑啉酰基硫脲类化合物的 IC50 值显示，5b 和 5g 是强效的脲酶抑制剂。化合物 5b 是一种强效的 α-葡萄糖苷酶抑制剂，化合物 5f 是一种强效的淀粉酶抑制剂，化合物 5b 则是一种强效的抗氧化剂。

  DOI：

  10.1039/d3ra06812a

文献信息

• Synthesis and structural characterization of new gold(I) complexes as bioactive and antitumor agents
  作者：L.B. de Oliveira、Lis R. V. Favarin、V.O. Araújo、N.L. Faganello、Heveline Silva、Amilcar Machulek Júnior、L.M.C. Pinto、Anderson R. L. Caires、D.F. Back、Lucas Pizzuti、Gleison Antônio Casagrande

  DOI：10.1016/j.poly.2021.115626

  日期：2022.2

  New mononuclear gold(I) complexes based on 1-thiocarbamoyl-3,5-diaryl-pyrazoline ligands were synthesized and structurally characterized using X-ray crystallography, 13C and 1H NMR studies, and elemental analysis combined with FT-IR and UV-Vis spectroscopy. Complexes 1–3 were prepared in good yields and characterized by X-ray diffraction as neutral mononuclear complexes of the [Au(L)Cl] type with linear

  合成了基于 1-硫代氨基甲酰基-3,5-二芳基-吡唑啉配体的新型单核金 (I) 配合物，并使用 X 射线晶体学、13 C 和1 H NMR 研究以及结合 FT-IR 和 UV 的元素分析对其进行了结构表征- 可见光谱。配合物1 - 3以良好的收率制备并通过X-射线衍射，与周围的Au线性协调几何[金（L）CL]类型的中性单核配合物予原子。制备的化合物的 UV-Vis 吸收曲线在 225 和 400 nm 之间表现出两个强吸收带，归因于 (M + X)LCT 类型的 HOMO → LUMO 电子跃迁（由金属加卤素引起的电荷转移激发到配体）和基于 DFT 研究的混合XLCT + IL 类型（由卤素到配体加内配体引起的电荷转移激发）。测定对 B16-F10 鼠黑色素瘤细胞、4 个 T1 鼠乳腺癌细胞和正常 BHK-21 幼仓鼠肾细胞系、复合物1 – 3 的抗肿瘤活性表现出比它们各自的游离配体更高的
• Synthesis and structural characterization of new heteroleptic copper(I) complexes based on mixed phosphine/thiocarbamoyl-pyrazoline ligands
  作者：Lis R.V. Favarin、Persiely P. Rosa、Lucas Pizzuti、Amilcar Machulek、Anderson R.L. Caires、L.S. Bezerra、L.M.C. Pinto、G. Maia、Claudia C. Gatto、Davi F. Back、Ademir dos Anjos、Gleison Antônio Casagrande

  DOI：10.1016/j.poly.2016.10.003

  日期：2017.1

  Abstract Two novel mononuclear heteroleptic Cu(I) complexes based on mixed phosphine/thiocarbamoyl-pyrazoline ligands were synthesized and structurally characterized. For both complexes, similar structural behavior was observed around Cu(I) atoms, which exhibited a distorted tetrahedral coordination geometry identified using τ4 parameter analysis. Interesting photophysical properties, including strong

  摘要合成了两种基于膦/硫代氨基甲酰基-吡唑啉混合配体的单核杂配Cu（I）配合物，并对其结构进行了表征。对于这两种配合物，在Cu（I）原子周围观察到相似的结构行为，这些行为表现出使用τ4参数分析确定的扭曲的四面体配位几何形状。在制备的化合物在λex= 290 nm激发时，在固态下观察到有趣的光物理性质，包括在UV-Vis光谱范围（200-450 nm）中的强吸收和橙红色发射。如TD-DFT研究所示，事实证明Cu（I）络合物的吸收和发射行为主要与HOMO和HOMO-1至LUMO（（M + X）LCT Cu（d10）→π*（SCN））跃迁有关。 。化合物的完整表征还包括X射线研究，元素分析，
• Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Ke-Ming Qiu、Hai-Hong Wang、Li-Ming Wang、Yin Luo、Xian-Hui Yang、Xiao-Ming Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.01.051

  日期：2012.3

  A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 mu M for EGFR and IC50 = 1.07 mu M for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 mu M, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.
• Microwave Assisted Synthesis of Thiocarbamoylpyrazoles and Application as an Alternative Latent Fingermark Developers
  作者：Bruno da Rosa、Dalila Venzke、Taís Poletti、Nathalia de Lima、Jeanifer Camacho、Kristiane Mariotti、Marco dos Santos、Lucas Pizzuti、Neftalí Carreño、Claudio Pereira

  DOI：10.21577/0103-5053.20200014

  日期：——

  Fingerprints are unique to each individual, contributing to human identification in forensic cases. The powder technique being widely used is considered one of the most important in latent fingermarks analysis. In this sense, the present work aimed to synthesize 1-thiocarbamoyl-4,5-dihydro-1H-pyrazoles and apply them as powder agents to develop latent fingermarks. The compounds were prepared from an effective and green synthesis via the condensation of chalcones with thiosemicarbazide in ethanol under microwave irradiation. Pyrazoles were tested and compared with a standard white powder (Sirchie (R)) on glass surfaces using sebaceous and natural fingermarks so that molecule 2c has been shown to be more promising providing image clarity. The derivatives of pyrazoles were promising as an alternative latent fingermark, presenting high quality images for fingermarks, proving to be a great tool for forensic sciences.
• The first gold(I) complexes based on thiocarbamoyl-pyrazoline ligands: Synthesis, structural characterization and photophysical properties
  作者：Andressa Ferle、Lucas Pizzuti、Simone D. Inglez、Anderson R.L. Caires、Ernesto S. Lang、Davi F. Back、Alex F.C. Flores、Amilcar M. Júnior、Victor M. Deflon、Gleison Antônio Casagrande

  DOI：10.1016/j.poly.2013.07.007

  日期：2013.10

  Novel gold(1) complexes based on thiocarbamoyl-pyrazoline ligands were synthetized for the first time and their structural/photophysical properties were determined. Two new monocationic complexes of the type [(Ph)(3)PAu(L)]PF6 (L = 1-thiocarbamoyl-5-(4-halophenyl)-3-phenyl-pyrazoline) were prepared by reacting (Ph)(3)PAuCl and ligands in the presence of KPF6 in a 1:1:1 molar ratio in a MeOH/CH2Cl2 (1:1) medium in good yields. The two cationic units from both complexes possess similar structural behaviour around the Au(1) atom which presents a two-coordinate and an almost linear coordination geometry. It was found good correlation between absorption and emission spectra and the photophysical properties were described. The prepared complexes (1 and 2) are representative examples of Au(I)/d(10) compounds that present bluish luminescence in the solid state at room temperature when excited at ex = 320 nm. The bluish emission that appears at ca. 415 nm for both cationic complexes was tentatively assigned to the LMCT excitations arising from sulphur based orbitals to the Au(I) atom (S -> Au-P). Besides X-ray studies, the complete structural characterization of the prepared compounds also includes elemental analyses, IR spectroscopy, H-1 and C-13 NMR, UV-Vis absorption and luminescence studies. (C) 2013 Elsevier Ltd. All rights reserved.