2-thioxo-5-(4-chlorophenylmethylidene)-4-imidazolidinone | 280137-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-thioxo-5-(4-chlorophenylmethylidene)-4-imidazolidinone
• 英文别名: 5-(4-chlorobenzylidene)-2-thiohydantoin；(5Z)-5-[(4-chlorophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• CAS: 280137-25-9
• 化学式: C₁₀H₇ClN₂OS
• 分子量: 238.697
• InChiKey: QNVGUGFRTRAWCL-YVMONPNESA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-thioxo-5-(4-chlorophenylmethylidene)-4-imidazolidinone 在 sodium 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 N-<5-(4-chlorobenzylidene)-4-oxo-2-imidazolidinyl>glycine
  参考文献：
  名称：

  Structure and activity studies of glycine receptor ligands. Part 7. Structural remarks on arylidene–imidazoline-4-one glycinates and glycinamides

  摘要：

  To improve the physicochemical properties (lipophilicity) of the potential ligands of glycine binding site of NMDA receptor, esters and amides of glycine derivatives of arylidene-imidazolidine-4-ones were obtained. The analysis of their properties (X-ray crystallography, NMR Spectral data and theoretical calculations) was performed with respect to the existence of the probable tautomeric forms. Their possible interaction with hypothetical active points of the receptor (taking into the account the model of glycine binding site of NMDA receptor) was discussed on the basis of simulation with IsoStar. program. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(01)00584-1
• 作为产物：
  描述：

  ethyl (2Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以1.07 g的产率得到2-thioxo-5-(4-chlorophenylmethylidene)-4-imidazolidinone
  参考文献：
  名称：

  The Synthesis of 2-Alkylthio-3-alkyl-5-arylmethylidene4H-imidazol-4-ones

  摘要：

  2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH3 in water).

  DOI：

  10.1080/10426500600614147

文献信息

• 5-Arylideneimidazolones with Amine at Position 3 as Potential Antibiotic Adjuvants against Multidrug Resistant Bacteria
  作者：Aneta Kaczor、Karolina Witek、Sabina Podlewska、Joanna Czekajewska、Annamaria Lubelska、Ewa Żesławska、Wojciech Nitek、Gniewomir Latacz、Sandrine Alibert、Jean-Marie Pagès、Elżbieta Karczewska、Katarzyna Kieć-Kononowicz、Jadwiga Handzlik

  DOI：10.3390/molecules24030438

  日期：——

  evaluated for compound 9. Most of the tested compounds reduced significantly (4-32-fold) oxacillin MIC in highly resistant MRSA HEMSA 5 strain. The anthracene-morpholine derivative (16) was the most potent (32-fold reduction). The tested compounds displayed significant EPI properties during RTE assay (37–97%). The naphthyl-methylpiperazine derivative 9 showed the most potent “dual action” of both oxacillin

  寻找新的细菌多药耐药（MDR）化学增敏剂，化学修饰（Z）-5-（4-氯亚苄基）-2-（4-甲基哌嗪-1-基）-3H-咪唑-4（5H）-one（ 6) 进行。设计并合成了在第 5 位具有稠合芳环的新化合物 (7-17)。晶体 X 射线分析证明，由于分子内 Dimroth 重排，最终化合物 (7-17) 在 3 位被叔胺-丙基部分和在 2 位被伯胺基团取代。评估了新化合物在革兰氏阳性菌或革兰氏阴性菌中的抗生素佐剂特性。在实时外排 (RTE) 测定中研究了外排泵抑制剂 (EPI) 对产气肠杆菌 (EA289) 中 AcrAB-TolC 泵的特性。应用对接和分子动力学来估计化合物 6-17 与青霉素结合蛋白 (PBP2a) 的相互作用。评估了化合物 9 的体外 ADME-Tox 特性。大多数测试化合物在高度抗性 MRSA HEMSA 5 菌株中显着降低了苯唑西林 MIC（4-32 倍）。蒽-吗啉衍生物
• Bicyclic imidazole-4-one derivatives: a new class of antagonists for the orphan G protein-coupled receptors GPR18 and GPR55
  作者：V. Rempel、K. Atzler、A. Behrenswerth、T. Karcz、C. Schoeder、S. Hinz、M. Kaleta、D. Thimm、K. Kiec-Kononowicz、C. E. Müller

  DOI：10.1039/c3md00394a

  日期：——

  GPR18 and GPR55 are orphan G protein-coupled receptors (GPCRs) that interact with certain cannabinoid (CB) receptor ligands.

  GPR18和GPR55是孤儿G蛋白偶联受体（GPCRs），它们与特定的大麻素（CB）受体配体相互作用。
• SYNTHESIS, CONFORMATIONAL ANALYSIS AND ANTITUMOR TESTING OF 5-(<i>Z</i>)-ARYLIDENE-4-IMIDAZOLIDINONE DERIVATIVES
  作者：A. I. Khodair、H. I. El-subbagh、A. M. Al-obaid

  DOI：10.1080/10426509808035741

  日期：1998.9.1

  5-(Z)-arylidene-3-aminomethyl-2-thioxo-4-imidazolidinones 42–55 and 5-(Z)-arylidene-3-aminomethyl-2-methylmercapto-4-imidazolidinones 56–67 have been synthesized via two different routes. Conformational analysis and antitumor activities have been studied. The antitumor activity of these compounds showed broad spectrum of activity against a wide range of different human cell lines of nine tumor subpanels

  摘要 一系列 5-(Z)-arylidene-2-amino-4-imidazolidinones 16–34, 5-(Z)-arylidene-2-(2-carboxyphenylamino)-4-imidazolidinones 35–41, 5-(Z) )-arylidene-3-aminomethyl-2-thioxo-4-imidazolidinones 42–55 和 5-(Z)-arylidene-3-aminomethyl-2-methylmercapto-4-imidazolidinones 56–67 已通过两种不同的途径合成。已经研究了构象分析和抗肿瘤活性。这些化合物的抗肿瘤活性显示出对九个肿瘤亚组的多种不同人类细胞系的广谱活性，导致细胞抑制和细胞毒性效力。
• Structure and activity studies of glycine receptor ligands. Part 8. Arylidene-imidazoline-4-one aminoacids
  作者：Janina Karolak-Wojciechowska、Agnieszka Mrozek、Katarzyna Kieć-Kononowicz、Jadwiga Handzlik

  DOI：10.1016/s0022-2860(02)00568-9

  日期：2003.4

  Abstract Based on chemical and preliminary biological experiments (inhibition to glycine receptor), structure and activity relationship of arylidene-imidazoline-4-one amino acids has been studied. In the course of our work, the simulation of the hydrogen bonds formation between ligand molecule and hypothetical receptor has been designed. Computed interactions are going to simulate possible ligand–receptor

  摘要 基于化学和初步生物学实验（对甘氨酸受体的抑制），研究了亚芳基咪唑啉4-1氨基酸的结构和活性关系。在我们的工作过程中，设计了配体分子和假设受体之间氢键形成的模拟。计算的相互作用将模拟可能的配体 - 受体与选定氨基酸的相互作用（在本研究中 - 使用碱性赖氨酸和酸性天冬氨酸）。获得的模型粗略估计了氨基酸与配体分子的结合能。提议的氨基酸结合能与异构苯亚甲基-咪唑啉-4-one 甘氨酸和α-丙氨酸的活性大致一致，其在苯亚甲基部分中以 m -Cl> p -Cl> o -Cl 取代基的顺序降低。
• Synthesis of dispirooxindoles containing N-unsubstituted heterocyclic moieties and study of their anticancer activity
  作者：A. A. Beloglazkina、N. A. Karpov、S. R. Mefedova、V. S. Polyakov、D. A. Skvortsov、M. A. Kalinina、V. A. Tafeenko、A. G. Majouga、N. V. Zyk、E. K. Beloglazkina

  DOI：10.1007/s11172-019-2511-6

  日期：2019.5

  A convenient method is proposed for the synthesis of N-unsubstituted spiroxindoles with different heterocyclic moieties (2-thiohydantoin, hydantoin, and thiazolidine) by the regio-selective 1,3-dipolar cycloaddition of azomethine ylides, generated from isatins and sarcosine, to arylidene derivatives of corresponding heterocycles. The cytotoxicity of compounds was tested by the MTT method against MCF7

  提出了一种方便的方法来合成具有不同杂环部分（2-硫代乙内酰脲、乙内酰脲和噻唑烷）的 N-未取代的螺吲哚，通过由靛红和肌氨酸生成的偶氮甲碱叶立德的区域选择性 1,3-偶极环加成与亚芳基相应杂环的衍生物。化合物的细胞毒性通过 MTT 法对 MCF7、A549、HEK 和 VA13 细胞系进行测试，并与抗癌药物 Nutlin-3a 进行比较。观察到基于乙内酰脲的二螺吲哚啉酮的最佳生物活性，最具细胞毒性的化合物对 A549 肺癌细胞具有选择性，IC50 值为 6.6±1.6 μmol L-1。

表征谱图