3-[(4-甲基苯基)甲基]-1,3-噻唑烷-2,4-二酮 | 103986-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-[(4-甲基苯基)甲基]-1,3-噻唑烷-2,4-二酮
• 英文名称: 3-(4-methyl-benzyl)-thiazolidine-2,4-dione
• 英文别名: 3-(4'-methylbenzyl)thiazolidin-2,4-dione；3-(4-methylbenzyl)thiazolidine-2,4-dione；3-(4-Methyl-benzyl)-thiazolidin-2,4-dion；2,4-Thiazolidinedione, 3-[(4-methylphenyl)methyl]-；3-[(4-methylphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 103986-16-9
• 化学式: C₁₁H₁₁NO₂S
• mdl: MFCD03614561
• 分子量: 221.28
• InChiKey: LCWXKXQNPIDGOK-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±45.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4-甲基苯基)甲基]-1,3-噻唑烷-2,4-二酮 在 哌啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (Z)-5-(4-((4-chlorophenyl)amino)benzylidene)-3-(4-methylbenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Integrated fragment-based drug design and virtual screening techniques for exploring the antidiabetic potential of thiazolidine-2,4-diones: Design, synthesis and in vivo studies

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115826
• 作为产物：
  描述：

  1,3-thiazolidine-2,4-dione potassium salt 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到3-[(4-甲基苯基)甲基]-1,3-噻唑烷-2,4-二酮
  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

文献信息

• Synthesis and <i>in vitro</i> cytotoxicity evaluation of β-carboline-linked 2,4-thiazolidinedione hybrids: potential DNA intercalation and apoptosis-inducing studies
  作者：Ramya Tokala、Sowjanya Thatikonda、Sravani Sana、Phanindranath Regur、Chandraiah Godugu、Nagula Shankaraiah

  DOI：10.1039/c8nj03248c

  日期：——

  19e was found to exhibit promising cytotoxic effects against triple negative breast cancer cell line (MDA-MB-231) with IC50 value of 0.97 ± 0.13 μM. Hence, further mechanistic studies of the apoptosis-inducing effect of 19e were conducted on the MDA-MB-23 cell line. Moreover, characteristic apoptotic features such as membrane blebbing, chromatin condensation, and apoptotic body formation were observed

  一系列新的β咔啉噻唑烷二酮的杂交合成并评估在体外针对选定的人癌症细胞系，细胞毒性潜力即，PC-3，A549，MG-63，HCT-15，MDA-MB-231，A431，和PANC-1以及正常的人类细胞系（L-132）。在这个新系列中，发现化合物19e对三阴性乳腺癌细胞系（MDA-MB-231）表现出有希望的细胞毒性作用，IC 50值为0.97±0.13μM。因此，对MDA-MB-23细胞系进行了19e的凋亡诱导作用的进一步机理研究。此外，在19e的作用下，观察到了特征性的凋亡特征，如膜起泡，染色质凝结和凋亡小体形成。使用AO / EB和DAPI染色对MDA-MB-231细胞进行染色。Annexin V-Alexa面粉488 / PI分析证实了明显的早期凋亡诱导作用。值得注意的是，DCFDA分析表明19e诱导了ROS的产生。此外，通过19e的JC-1染色观察到线粒体膜电位塌陷。此外，细胞周期分
• Synthesis and structural elucidation of new benzylidene imidazolidines and acridinylidene thiazolidines
  作者：T.G. SILVA、F.S.V. BARBOSA、S.S.F. BRANDÃO、M.C.A. LIMA、S.L. GALDINO、I.R. PITTA、J. BARBE

  DOI：10.1515/hc.2001.7.6.523

  日期：2001.1

  New benzylidene imidazolidine and acridinylidene thiazolidine derivatives were prepared from substituted imidazolidinones and substituted thio-imidazolidinones either by nucleophilic addition on cyanoacrylates or by condensation with arylaldehydes. Introduction It has been shown since a long time that acridines and azolidines are efficient drugs in infectious diseases. Thus we intended to prepare some

  通过在氰基丙烯酸酯上亲核加成或通过与芳醛缩合，由取代的咪唑啉酮和取代的硫代咪唑啉酮制备新的亚苄基咪唑烷和吖啶亚基噻唑烷衍生物。引言 长期以来，吖啶和唑烷已被证明是治疗传染病的有效药物。因此我们打算制备一些相应的缩合衍生物，以期获得具有协同作用的新药[1-5]。结果与讨论 3-(4'-Bromo-benzyl)-4-thio-5-benzylidene-imidazolidin-2-ones, 4 and 5, l-methyl-3-(4'chloro-benzyl)-5-benzylidene- imidazolidin-2-ones, 8 和 9, 和 l-methyl-2-thio-5-(4"bromo-benzylidene) imidazolidin-4-one, 1_1, 是通过两种不同的一般路线制备的。使用的第一个过程是 3-(4'-bromo-benzyl)-4-thio-imidazolidin-2one
• Thiazolidine derivatives: In vitro toxicity assessment against promastigote and amastigote forms of Leishmania infantum and ultrastructural study
  作者：Allana L.A. Gouveia、Fábio A.B. Santos、Luiz C. Alves、Iranildo José Cruz-Filho、Paula R. Silva、Iris T.T. Jacob、José Cleberson S. Soares、Dayane K.D.N. Santos、Tulio Ricardo C.L. Souza、Jamerson F. Oliveira、Maria do Carmo A. Lima

  DOI：10.1016/j.exppara.2022.108253

  日期：2022.5

  to evaluate in vitro two series of thiazolidine compounds (7a-7e and 8a-8e) against Leishmania infantum. We performed in vitro evaluations through macrophage cytotoxicity assays (J774) and nitric oxide production, activity against promastigotes and amastigotes, as well as ultrastructural analyzes in promastigotes. In the evaluation of cytotoxicity, the thiazolidine compounds presented CC50 values between

  被忽视的疾病，如利什曼病，是一组主要发生在热带国家的传染病。被认为是治疗有限的公共卫生问题。因此，需要新的疗法。从这个意义上说，我们的建议是在体外评估两个系列的噻唑烷化合物（7a-7e 和 8a-8e）对抗婴儿利什曼原虫。我们通过巨噬细胞细胞毒性测定 (J774) 和一氧化氮产生、对前鞭毛体和无鞭毛体的活性以及前鞭毛体的超微结构分析进行了体外评估。在细胞毒性评价中，噻唑烷化合物呈 CC 50值在 8.52 和 126.83 μM 之间。关于针对前鞭毛体形式的评估，IC 50值介于 0.42 和 142.43 μM 之间。化合物 7a 是最有希望的，因为它的 IC 50最低。用化合物7a处理的寄生虫表现出细胞体收缩、鞭毛缩短和丧失、线粒体严重水肿和细胞质空泡化等变化，导致寄生虫细胞不存活。在针对无鞭毛体形式的测定中，该化合物显示出低 IC 50 (0.65 μM)。这些结果表明化合物 7a
• Synthesis and Biological Activity of Novel Acridinylidene and Benzylidene thiazolidinediones
  作者：R.H. Mourão、T.G. Silva、A.L.M. Soares、E.S. Vieira、J.N. Santos、M.C.A. Lima、V.L.M. Lima、S.L. Galdino、J. Barbe、I.R. Pitta

  DOI：10.1016/j.ejmech.2005.06.002

  日期：2005.11

  A novel set of acridinylidene thiazolidinediones and benzylidene thiazolidinediones was synthesized by nucleophilic addition of cyanoacrylates. Some of these compounds were evaluated for their glucose lowering capability and their effects on the triglyceride level in alloxan diabetic mice. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives
  作者：Francisco W.A. Barros、Teresinha Gonçalves Silva、Marina Galdino da Rocha Pitta、Daniel P. Bezerra、Letícia V. Costa-Lotufo、Manoel Odorico de Moraes、Cláudia Pessoa、Maria Aline F.B. de Moura、Fabiane C. de Abreu、Maria do Carmo Alves de Lima、Suely Lins Galdino、Ivan da Rocha Pitta、Marilia O.F. Goulart

  DOI：10.1016/j.bmc.2012.04.007

  日期：2012.6

  Although their exact role in controlling tumour growth and apoptosis in humans remains undefined, acridine and thiazolidine compounds have been shown to act as tumour suppressors in most cancers. Based on this finding, a series of novel hybrid 5-acridin-9-ylmethylene-3-benzyl-thiazolidine-2,4-diones were synthesised via N-alkylation and Michael reaction. The cell viability was analysed using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, and DNA interaction assays were performed using electrochemical techniques. (C) 2012 Elsevier Ltd. All rights reserved.