3-(4-甲基苯基)-2-硫酮-1,3-噻唑啉-4-酮 | 3919-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-甲基苯基)-2-硫酮-1,3-噻唑啉-4-酮
• 中文别名: 3-对甲苯基罗丹宁
• 英文名称: 3-phenyl-2-thioxothiazolidin-4-one
• 英文别名: 3-(4-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one；2-thioxo-3-p-tolylthiazolidin-4-one；2-thioxo-3-N,(4-methylphenyl)thiazolidine-4-one；3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 3919-81-1
• 化学式: C₁₀H₉NOS₂
• mdl: MFCD00268237
• 分子量: 223.32
• InChiKey: UFIUHRONJXVXHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(4-甲基苯基)-2-硫酮-1,3-噻唑啉-4-酮 在 sodium tungstate 、 双氧水 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以14%的产率得到3-(4-methylphenyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture

  摘要：

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

  DOI：

  10.1021/jm400828u
• 作为产物：
  描述：

  4-甲基苯胺盐酸盐 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.25h， 生成 3-(4-甲基苯基)-2-硫酮-1,3-噻唑啉-4-酮
  参考文献：
  名称：

  Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy

  摘要：

  Different inflammatory diseases and allergic reactions are mediated by leukotrienes, which arise from the oxygenation of arachidonic acid catalyzed by 5-lipoxygenase (5-LO). One promising approach for an effective anti-leukotriene therapy is the inhibition of this key enzyme. This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Through optimization of C06, evaluation of structure activity relationships including profound assessment of the thiazolone core and consideration of the solubility, the 5-benzyl-2-phenyl-4-hydroxythiazoles represented by 46 (ST-1829, 5-(4-chlorobenzyl)-2-p-tolylthiazol-4-ol) were developed. Compound 46 showed an improved 5-LO inhibitory activity in cell-based (IC50 values 0.14 mu M) and cell-free assays (IC50 values 0.03 mu M) as well as a prominent enhanced solubility. Furthermore, it kept its promising inhibitory potency in the presence of blood serum, excluding excessive binding to serum proteins. These facts combined with the non-cytotoxic profile mark a major step towards an effective anti-inflammatory therapy. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.054

文献信息

• Synthesis and Reactions of Some Pyrazine Derivatives
  作者：A. K. El-Shafei、A. M. El-Sayed、H. Abdel-Ghany、A. M. M. El-Saghier

  DOI：10.1080/00397919408010198

  日期：1994.7

  Abstract The pharmacodynamic properties1-3 of substituted amino pyrazines as well as their importance in the synthesis of pteridine and other polyfused heterocyclic systems is well known4,5. In this investigation we aim to prepare a new series of condensed heterocyclic systems containing the pyrazine nucleus.

  摘要 取代氨基吡嗪的药效学特性 1-3 以及它们在合成蝶啶和其他多稠合杂环系统中的重要性是众所周知的 4,5。在这项研究中，我们的目标是制备一系列新的含有吡嗪核的稠合杂环系统。
• Synthesis and supramolecular self-assembly of thioxothiazolidinone derivatives driven by H-bonding and diverse π–hole interactions: A combined experimental and theoretical analysis
  作者：Hina Andleeb、Imtiaz Khan、Antonio Bauzá、Muhammad Nawaz Tahir、Jim Simpson、Shahid Hameed、Antonio Frontera

  DOI：10.1016/j.molstruc.2017.03.046

  日期：2017.7

  (AIM) and NCIplot. The computation of the energy features of the diverse noncovalent interactions including C H⋯π, π⋯π and lp⋯π-hole interactions revealed their conspicuous role in the stabilization of the three-dimensional supramolecular frameworks for both compounds in addition to the C H⋯O/S H-bonding interactions.

  摘要 通过 3-(4-aryl)-2-thioxo-1 的 Knoevenagel 缩合反应合成了两种新的 3-aryl-5-(4-nitrobenzylidene)-2-thioxothiazolidin-4-one 衍生物 (1 & 2), 3-thiazolidin-4-ones 与 4-硝基苯甲醛。两种产物均以良好的收率分离为橙色结晶固体，并通过分析、光谱和结构方法进行了充分表征。通过密度泛函理论 (DFT) 计算 (M06-2X/def2-TZVP)、分子静电势 (MEP) 表面分析在固态中观察到的标题化合物的有趣超分子组装，并通过巴德的“分子中的原子”（AIM）和 NCIplot。包括CH⋯π在内的多种非共价相互作用的能量特征的计算，
• Identification of novel pyrazole–rhodanine hybrid scaffolds as potent inhibitors of aldose reductase: design, synthesis, biological evaluation and molecular docking analysis
  作者：Hina Andleeb、Yildiz Tehseen、Syed Jawad Ali Shah、Imtiaz Khan、Jamshed Iqbal、Shahid Hameed

  DOI：10.1039/c6ra14531k

  日期：——

  NMR) and mass spectrometry. The hybrid compounds were evaluated as aldehyde and aldose reductase inhibitors. The biological screening results identified several compounds as remarkable inhibitors of ALR1 and ALR2. Among them, compounds 9c and 9k showed excellent activity (and complete selectivity) towards the aldose reductase enzyme with IC50 values of 1.22 ± 0.67, and 2.34 ± 0.78 μM, respectively, as

  为了开发新型的有效醛糖还原酶抑制剂，设计并合成了一系列1,3-二芳基吡唑同化的3-取代的4-oxo-2-thioxo-1,3-thiazolidines（9a–n）。通过药效基团整合方法获得了良好或优异的产量。新合成的吡唑-若丹宁衍生物的结构是通过容易获得的光谱方法（FTIR，1 H和13 C NMR）和质谱确定的。杂合化合物被评估为醛和醛糖还原酶抑制剂。生物学筛选结果确定了几种化合物是ALR1和ALR2的显着抑制剂。其中，化合物9c和9k与标准药物（山梨醇; IC 50 = 3.10±0.20μM）相比，对醛糖还原酶具有优异的活性（完全选择性），IC 50值分别为1.22±0.67和2.34±0.78μM 。进行了最有效的抑制剂9c的分子对接分析，以鉴定酶活性口袋内部的假定结合模式。据信，这些新发现的醛糖还原酶抑制剂代表有价值的先导结构，可进一步简化候选化合物的产生，以针对多种病理状况，最令人震惊的是长期的糖尿病并发症。
• A New Synthesis Strategy for Rhodanine and Its Derivatives
  作者：Zhenliang Pan、Wankai An、Lulu Wu、Liangxin Fan、Guoyu Yang、Cuilian Xu

  DOI：10.1055/a-1485-5925

  日期：2021.7

  Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N-aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid,

  罗丹宁及其衍生物由于其广泛的生物活性而在药理学研究中被称为特权结构，但罗丹宁骨架的合成方法受到限制。本文通过质子酸催化硫脲与巯基乙酸的反应，不仅可以直接制备罗丹宁骨架，而且可以直接制备N-芳基罗丹宁，为罗丹宁及其衍生物的合成提供了一种新途径。所开发的策略是简单，高效，原子经济的，并且产率高。
• Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one
  作者：T. Bensafi、D. Hadji、A. Yahiaoui、K. Argoub、A. Hachemaoui、A. Kenane、B. Baroudi、K. Toubal、A. Djafri、A. M. Benkouider

  DOI：10.1080/17415993.2021.1951729

  日期：2021.11.2

  their dipole moment, linear polarizability, and first hyperpolarizability to elucidate the nonlinear optical (NLO) activity. The HOMO–LUMO energy gap obtained from the PBE0 functional agrees with the experimental data deduced from the UV–VIS measurement. The resulting compound shows a high hyper-Rayleigh scattering (HRS) first hyperpolarizability, which makes it suitable for optoelectronic and optical

  在本研究中，我们报告了 (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one 的联合实验和理论研究，该研究通过罗丹宁与芳香醛的 Knoevenagel 缩合合成。良到极好的产量。多种物理化学技术用于表征合成的化合物，包括1 H 和13C 核磁共振 (NMR)、扫描电子显微镜 (SEM)、能量色散 X 射线分析 (EDX) 和紫外-可见 (UV-VIS) 光谱。使用密度泛函理论 (DFT) 方法在不同泛函 (B3LYP、CAM-B3LYP、M05-2X、PBE0 和 ωB97X- D) 结合不同的基组。我们还计算了它们的偶极矩、线性极化率和第一超极化率，以阐明非线性光学 (NLO) 活动。从 PBE0 泛函获得的 HOMO-LUMO 能隙与从 UV-VIS 测量推导出的实验数据一致。所得化合物显示出高超瑞利散射 (HRS)