5-[(6-methyl-4-oxo-4H-chromen-3-yl)methylene]thiazolidine-2,4-dione | 1093128-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-[(6-methyl-4-oxo-4H-chromen-3-yl)methylene]thiazolidine-2,4-dione
• 英文别名: 5-[(6-Methyl-4-oxochromen-3-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1093128-11-0
• 化学式: C₁₄H₉NO₄S
• 分子量: 287.296
• InChiKey: WPOCVLITZMUDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(6-methyl-4-oxo-4H-chromen-3-yl)methylene]thiazolidine-2,4-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 以65%的产率得到5[(6-methyl-4-oxo-4H-chromen-3yl)methyl]thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression

  摘要：

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.034
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 在 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 反应 12.0h， 生成 5-[(6-methyl-4-oxo-4H-chromen-3-yl)methylene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression

  摘要：

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.034

文献信息

• 6-Methyl 3-chromonyl 2,4-thiazolidinedione/2,4-imidazolidinedione/2-thioxo-imidazolidine-4-one compounds: novel scavengers of reactive oxygen species
  作者：Paweł Berczyński、Ewa Duchnik、Irena Kruk、Teresa Piechowska、Hassan Y. Aboul-Enein、Oya Bozdağ-Dündar、Meltem Ceylan-Unlusoy

  DOI：10.1002/bio.2554

  日期：2014.6

  chemiluminescence, electron paramagnetic resonance, spin trapping and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH•) methods. The total antioxidant capacity was also measured using a ferric‐ferrozine reagent. Compounds having a hydrogen atom at the N3‐position of the β‐ring were effective in quenching CL resulted from the KO2/18‐crown‐6‐ether system (a source of superoxide anion radical, ) in a dose‐dependent

  抗氧化剂对人体健康的好处通常归因于其潜在的去除活性氧的能力，从而提供抗氧化应激的保护。本文首次通过化学发光，电子顺磁共振，自旋俘获和2,2-二苯基-1-吡咯并肼基（DPPH •）评估了九种6-甲基3-苯甲酰基衍生物（CM）的自由基清除活性。方法。总抗氧化剂容量也使用铁-铁嗪试剂测量。在β环N3位具有氢原子的化合物可有效地猝灭由KO 2 / 18-冠冕-6-醚系统（超氧阴离子自由基的来源）产生的CL ，且剂量依赖性0.05–1 mmol / L的范围[IC 50范围从0.353（0.04）到0.668（0.05）mmol / L]。所研究的化合物对Fenton反应产生的羟基自由基（HO • HO •）具有明显的清除作用，浓度为2.5 mmol / L时，范围为24.0％至61.0％。此外，还发现所检测的化合物可抑制DPPH •，在相同浓度下，其抑制范围为51.9％至97.4％。另外，总抗氧化
• Synthesis and aldose reductase inhibitory activity of some new chromonyl-2,4-thiazolidinediones
  作者：Oya Bozdağ-Dündar、Begüm Evranos、Net Daş-Evcimen、Mutlu Sarıkaya、Rahmiye Ertan

  DOI：10.1016/j.ejmech.2008.01.004

  日期：2008.11

  As it is known that still, there were no any confident ARIs on the market and they have several side effects, we need to approve new ARIs to reduce diabetic complications especially which have effect on the cataract formation. In this study, a new series of chromonl-2,4-thiazolidinediones (Ia-e, IIa-e, IIIa-e) were prepared by Knoevenagel reaction with substituted 3-formylchromones (3a-e) and unsubstituted (1) or substituted 2,4-thiazolidinedione (2). The synthesized compounds were tested for their ability to inhibit rat kidney AR by an in vitro spectrophotometric assay. Compound IIIe showed the highest inhibitory activity (82.43 +/- 0.76%). Compounds la-e and IIIa-d also showed significant inhibitory activity (42.40 +/- 5.78, 52.71 +/- 3.31, 49.69 +/- 1.55, 50.80 +/- 3.62, 46.70 +/- 2.33, 49.44 +/- 4.53, 61.17 +/- 4.74, 68.58 +/- 2.05, 77.28 +/- 0.26%, respectively). (C) 2008 Elsevier Masson SAS. All rights reserved.