(Z)-5-(3-硝基苯亚甲基)噻唑烷-2,4-二酮 | 1055980-73-8

• 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: (Z)-5-(3-硝基苯亚甲基)噻唑烷-2,4-二酮
• 英文名称: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione
• 英文别名: (Z)-5-(3-nitrobenzylidene)thiazolidine-2,4-dione；5-(3'-nitrobenzylidene)thiazolidine-2,4-dione；5-[(3-Nitrophenyl)methylene]-1,3-thiazolane-2,4-dione；(5Z)-5-[(3-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1055980-73-8
• 化学式: C₁₀H₆N₂O₄S
• 分子量: 250.235
• InChiKey: HWOVMANHBOBQRW-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  117
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-(3-硝基苯亚甲基)噻唑烷-2,4-二酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以78%的产率得到(Z)-5-(3-nitrobenzylidene)-3-benzylthiazolidine-2,4-dione
  参考文献：
  名称：

  Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione

  摘要：

  Hybridization of two different bioactive molecules with different mechanism of action is one of the methods that are being adopted to treat cancer. Molecules bearing a thiazolidine-2,4-dione scaffold have been recognized as antineoplastic agents with a broad spectrum of activity against many cancer cell lines. In this manuscript we have described the synthesis and biological evaluation of two series of N-3-substituted-5-arylidene thiazolidine-2,4-diones, bearing the alpha-bromoacryloylamido moiety at the para- or meta-position on the phenyl of the arylidene portion. We have observed that selected compounds 5a, 5c and 5g suppress proliferation of human myeloid leukaemia HL-60 and U937 cells by triggering morphological changes and internucleosomal DNA fragmentation, which are well-known features of apoptosis. Finally, our results indicated that the investigated compounds induced apoptotic cell death through a mechanism that involved activation of multiple caspases and was also associated with the release of cytochrome c from the mitochondria. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.030
• 作为产物：
  描述：

  (5Z)-4-(2-hydroxyethylamino)-5-[(3-nitrophenyl)methylidene]-1,3-thiazol-2-one 生成 (Z)-5-(3-硝基苯亚甲基)噻唑烷-2,4-二酮
  参考文献：
  名称：

  PLEVACHUK, N. E.;ZIMENKIVSKIJ, B. S.;GALKEVICH, I. J.;STEBLYUK, P. M., FARMATSEVTICHNIJ ZH., 1981, N 4, 40-43, 80

  摘要：

  DOI：

文献信息

• Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies
  作者：Varinder Singh、Amanjot Singh、Gagandeep Singh、Raman K. Verma、Rajiv Mall

  DOI：10.1007/s00044-021-02781-y

  日期：2021.10

  Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral studies. In addition, all compounds were screened for α-glucosidase inhibitory activity and further supported by molecular docking studies carried out at the active site

  合成了具有噻唑烷二酮、罗丹宁、乙内酰脲和硫代乙内酰脲部分的苯并恶唑连接的间位和对位取代的新化学实体 ( 5a – 5h )，并通过1 H NMR、13 C NMR、FT-IR 和 HRMS 光谱研究表征。此外，与用作标准药物的阿卡波糖相比，所有化合物都筛选了 α-葡萄糖苷酶抑制活性，并得到了在 α-葡萄糖苷酶活性位点（PDB 代码：3TOP）的分子对接研究的进一步支持。在八种测试化合物中，发现5d是最有效的 α-葡萄糖苷酶抑制剂 (IC 50 = 9.48 ± 0.36 µM)，在苯环的间位取代了罗丹宁部分。
• Pharmaceutical Preparations Comprising Insulin, Zinc Ions and Zinc-Binding Ligand
  申请人：Kaarsholm Niels Christian

  公开号：US20090123563A1

  公开（公告）日：2009-05-14

  Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

  这段话的中文翻译如下：使用分支配体的新型制备物，用于R-状态胰岛素六聚体的HisB10 Zn2+位点。这些制备物具有长效作用，旨在为灵活的注射方案设计。
• Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines
  作者：Elodie Cortelazzo-Polisini、Michel Boisbrun、Axel Hans Gansmüller、Corinne Comoy

  DOI：10.1021/acs.joc.2c00748

  日期：2022.8.5

  photoinduced isomerization of a series of arylidene heterocycles 1. The photoreaction mechanism was investigated by a combined UV–vis/photo-NMR spectroscopic study, and we showed that Ar-TZDs exhibit a positive P-type photochromism, which limits their isomerization efficiency. By exploring the solvatochromism in a series of solvents, the conditions favoring the conversion toward one or the other stereoisomer

  我们在此报告了一系列亚芳基杂环1的光致异构化。通过结合 UV-vis/photo-NMR 光谱研究研究了光反应机理，我们发现 Ar-TZD 表现出正 P 型光致变色，这限制了它们的异构化效率。通过探索一系列溶剂中的溶剂致变色，研究了有利于向一种或另一种立体异构体转化的条件，特别是通过选择合适的波长。最后，通过方便地制备各种稠合杂环喹啉并以良好的总产率提出了该光异构化研究的扩展。
• 10.1007/s11030-024-10853-5
  作者：Rukyanaik、Gamidi, Rama Krishna、Kumari, Jyothi、Sriram, Dharmarajan、Basavoju, Srinivas

  DOI：10.1007/s11030-024-10853-5

  日期：——

  A simple and effective three-component one-pot green methodology was employed for the synthesis of a new thiazolidine-2,4-dione based bisspirooxindolo-pyrrolidine derivatives using [Bmim]BF4 ionic liquid via [3 + 2] cycloaddition reaction. It is an environmentally benign, column chromatography-free, shorter reaction time, good yield and easy product isolation method. The synthesized compounds 10a–x

  采用简单有效的三组分一锅法绿色方法，使用[Bmim]BF 4离子液体通过[3 + 2]环加成反应合成新型噻唑烷-2,4-二酮基双螺氧吲哚并吡咯烷衍生物。它是一种环境友好、无需柱层析、反应时间短、收率好、产物分离容易的方法。合成的化合物10a-x使用各种光谱方法（如 FT-IR、 1 H NMR、 13 C NMR、质谱）以及最后的单晶 X 射线衍射方法进行了彻底表征。对这些合成的化合物进行了体外抗结核（抗结核）活性研究，它们对结核分枝杆菌H37Rv 菌株表现出良好至中等的抗结核活性。化合物10a表现出良好的抗结核活性，MIC（最低抑制浓度）值为12.5μg/mL，化合物10m、10o和10r表现出中等活性，MIC值为25.0μg/mL。其余化合物对结核分枝杆菌的活性较差。使用乙胺丁醇、利福平和异烟肼作为标准药物。此外，对 TB 蛋白（PDB ID：1DF7）进行了计算机分子对接实验以了解结合相互作用，结果显示最小结合能值范围为
• Structure–activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors
  作者：Rosanna Maccari、Rosaria Ottanà、Carmela Curinga、Maria Gabriella Vigorita、Dietmar Rakowitz、Theodora Steindl、Thierry Langer

  DOI：10.1016/j.bmc.2005.02.026

  日期：2005.4

  The structure-activity relationships (SARs) of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors (ARIs) were extended by varying the substitution pattern on the 5-arylidene moiety and on N-3. In particular, the introduction of an additional aromatic ring or an H-bond donor group on the 5-benzylidene ring enhanced ALR2 inhibitory potency. Moreover, the presence of a carboxylic anionic chain on N-3 was shown to be an important, although not essential, structural requisite to produce high levels of ALR2 inhibition. The length of this carboxylic chain was critical and acetic acids 4 were the most effective inhibitors among the tested derivatives. Molecular docking simulations into the ALR2 active site accorded with the in vitro inhibition data. They allowed the rationalization of the observed SARs and provided a pharmacophoric model for this class of ARIs. (c) 2005 Elsevier Ltd. All rights reserved.