5-(4-nitro-benzylidene)-thiazolidine-2,4-dione | 177703-41-2

• 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: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione
• 英文别名: (5Z)-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione；(5Z)-5-(4-nitrobenzylidene)thiazolidine-2,4-dione；(Z)-5-(4-nitrobenzylidene)thiazolidine-2,4-dione；5-(4'-nitrobenzylidene)thiazolidine-2,4-dione；5-(4-nitrobenzylidene)thiazolidine-2,4-dione；(5Z)-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 177703-41-2
• 化学式: C₁₀H₆N₂O₄S
• 分子量: 250.235
• InChiKey: DWADLBIRAWMTCN-YVMONPNESA-N

物化性质

• 熔点：
  265.5 °C (decomp)
• 密度：
  1.595±0.06 g/cm3(Predicted)

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：

  5-(4-nitro-benzylidene)-thiazolidine-2,4-dione 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)-3-(4-tert-butylbenzyl)-5-(4-nitrobenzylidene)thiazolidine-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：

  对硝基苯甲醛 在 sodium hydrogensulfite 、 三氯氧磷 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Phosphoryl Chloride Mediated Synthesis of 5-Arylidene-2,4-Thiazolidinediones Derivatives via Aromatic Bisulfite Adducts

  摘要：

  通过芳香醛的亚硫酸氢盐加合物与噻唑烷-2,4-二酮的缩合反应形成碳-碳键以制备5-芳亚甲基-2,4-噻唑烷二酮的研究已经开展。这一新颖方法被应用于将取代的芳基亚硫酸氢盐加合物在较非极性溶剂如甲苯、氯苯和邻二甲苯中，使用POCl3转化为相应的5-芳亚甲基-2,4-噻唑烷二酮。5-(4-甲氧基苄叉基)噻唑烷-2,4-二酮和5-(4-乙氧基苄叉基)噻唑烷-2,4-二酮以良好产率获得。

  DOI：

  10.2174/15701786113106660081

文献信息

• Novel ligands for the hisb10 zn2+ sites of the r-state insulin hexamer
  申请人：——

  公开号：US20030229120A1

  公开（公告）日：2003-12-11

  Novel ligands for the HisB10 Zn 2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R-态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• Stabilised insulin compositions
  申请人：Kaarsholm Christian Niels

  公开号：US20050065066A1

  公开（公告）日：2005-03-24

  The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the His B10 Zn 2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.

  本发明提供了包含胰岛素和新型配体的药物组合物，用于R-态胰岛素六聚体的His B10 Zn2+位点。由此制备的药物具有改善的物理和化学稳定性。
• Green Synthesis, Biological Activity Evaluation, and Molecular Docking Studies of Aryl Alkylidene 2, 4-thiazolidinedione and Rhodanine Derivatives as Antimicrobial Agents
  作者：Malihe Akhavan、Naser Foroughifar、Hoda Pasdar、Ahmadreza Bekhradnia

  DOI：10.2174/1386207322666191127103122

  日期：2020.1.16

  FT-IR spectroscopy. The binding-free energy between compounds 10a and 10b with 3EEJ protein were found to be -8.08 kcal/mol and -8.15 kcal/mol, respectively. These compounds having a heteroaromatic ring attached to the TZD or rhodanine core showed excellent antimicrobial activity with MIC values of 0.25-8 μg/mL (compound 10a) and 0.5-16 μg/mL (compound 10b) against the most tested fungi strains, Gram-positive

  目的和目的魔术支架若丹宁和噻唑烷是药物设计和发现中非常重要的杂环化合物。这些是重要的杂环化合物，由于它们具有多种生物活性，包括抗菌，抗真菌，抗病毒，抗疟疾和抗炎活性，因此备受关注。这些试剂通常表现出选择性毒性。这项研究的目的是分子对接，绿色和无溶剂的新系列杂/芳族取代的若丹宁和噻唑烷类似物的有效合成，然后研究其抗菌活性。材料与方法在离子液体ChCl /脲的存在下，向TZD或罗丹宁（1 mmol）的混合物中添加各种醛（1 mmol）。反应完成后，过滤收集获得的粗化合物，并将产物从乙醇中重结晶。通过分子对接研究获得了所有合成的化合物与3EEJ蛋白（光滑念珠菌）之间的自由结合能。使用微量稀释法对（ATCC 6538）和（ATCC 12228）革兰氏阴性，（ATCC 8739）和（ATCC 9027）革兰氏阳性以及（ATCC 1012），（ATCC 339），C。（ATCC 1057）进行微稀释法评估），（ATCC
• [EN] PHARMACEUTICAL PREPARATIONS COMPRISING ACID-STABILISED INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE STABILISEE D'UN POINT DE VUE ACIDE
  申请人：NOVO NORDISK AS

  公开号：WO2004080480A1

  公开（公告）日：2004-09-23

  Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• Privileged Scaffolds or Promiscuous Binders: A Comparative Study on Rhodanines and Related Heterocycles in Medicinal Chemistry
  作者：Thomas Mendgen、Christian Steuer、Christian D. Klein

  DOI：10.1021/jm201243p

  日期：2012.1.26

  campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed

  罗丹宁和具有多个杂原子的相关五元杂环最近因在筛选活动中表现为“频繁的杀手”而成为非选择性化合物，因此在药物发现中几乎没有价值。但是，这种判断似乎主要是基于轶事证据。在筛选活动中鉴定出多种罗丹宁和相关化合物后，我们决定对它们的滥交进行系统的研究。合成了163种罗丹宁，乙内酰脲，硫代乙内酰脲和噻唑烷二酮，并针对几个目标进行了测试。还针对聚集和亲电反应性对化合物进行了表征，并分析了罗丹宁与相关化合物在已发表的X射线共晶结构中的结合模式。结果表明，环外，若丹宁和硫代乙内酰脲中的双键硫原子除具有其他结构特征外，还为极性相互作用和氢键提供了特别高的相互作用位点密度。这会导致“筛选范围”内浓度的混杂行为，但不应视为将此类筛选命中排除在进一步开发之外的一般剔除标准。建议将针对靶标亲和力和选择性的特殊标准应用于这些类型的化合物，并因此以有用的方式利用其特殊和潜在有价值的生物分子结合特性。这会导致“筛选范围”