5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione | 1006675-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
• 英文别名: 5-[(1,3-Diphenylpyrazol-4-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1006675-22-4
• 化学式: C₁₉H₁₃N₃O₂S
• 分子量: 347.397
• InChiKey: JQYPSRHCWYXONR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione 、 1-碘代丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3-propylthiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazolyl-2,4-thiazolidinediones as anti-inflammatory and neuroprotective agents

  摘要：

  Novel pyrazolyl-2,4-thiazolidinediones were prepared via the reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinediones and substituted benzyl-2,4-thiazolidinediones. The resultant compounds were first evaluated for their anti-inflammatory and neuroprotective properties in vitro. The active compounds were further studied in vivo by using the formalin-induced paw edema and the turpentine oil-induced granuloma pouch bioassays. We identified four novel compounds that showed protective effects in vitro at non-toxic concentrations, and were also effective in the animal models of acute and sub-acute inflammation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.021
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 1,3-二苯-1H-吡唑-4-甲醛 在 哌啶 作用下， 以 甲苯 为溶剂， 生成 5-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  带有吡唑部分的 NewN-3 取代的噻唑烷-2,4-二酮衍生物的合成和抗菌和细胞毒活性

  摘要：

  合成了两个新系列的带有吡唑部分的 N-3 取代的噻唑烷-2,4-二酮衍生物（5a-j 和 7a-j），并在体外评估了它们作为抗革兰氏阳性菌和革兰氏阴性菌的抗菌剂的功效。菌株。在测试的化合物中，发现 7b、7c、7i 和 7j 对革兰氏阳性菌（金黄色葡萄球菌和化脓性链球菌）具有活性，最小抑菌浓度 (MIC) 值在 6.25–25 µg/mL 范围内，并且一些化合物还针对耐甲氧西林金黄色葡萄球菌 (MRSA) 进行了测试。化合物 7c 和 7j 分别在 6.25 和 12.5 µg/mL 的 MIC 值下抑制 MRSA 的生长。还讨论了亲脂性 (C log P) 对所制备产品的生物特征 (MIC) 的影响。从构效关系研究的角度来看，据观察，这些化合物的亲脂特性对其抗菌活性至关重要。此外，对人宫颈癌细胞系 (HeLa) 和小鼠胚胎成纤维细胞系 (NIH 3T3) 的 MTT 细胞毒性研究结果表明，化合物

  DOI：

  10.1002/ardp.201300466

文献信息

• Synthesis and Antibacterial and Cytotoxic Activities of New<i>N</i>-3 Substituted Thiazolidine-2,4-dione Derivatives Bearing the Pyrazole Moiety
  作者：Nisheeth C. Desai、Hitesh M. Satodiya、Ghanshyam M. Kotadiya、Hasit V. Vaghani

  DOI：10.1002/ardp.201300466

  日期：2014.7

  Two new series of N‐3 substituted thiazolidine‐2,4‐dione derivatives bearing the pyrazole moiety (5a–j and 7a–j) were synthesized and assessed in vitro for their efficacy as antibacterial agents against gram‐positive and gram‐negative bacterial strains. Among the tested compounds, 7b, 7c, 7i, and 7j were found to be active against gram‐positive bacteria (Staphylococcus aureus and Streptococcus pyogenes)

  合成了两个新系列的带有吡唑部分的 N-3 取代的噻唑烷-2,4-二酮衍生物（5a-j 和 7a-j），并在体外评估了它们作为抗革兰氏阳性菌和革兰氏阴性菌的抗菌剂的功效。菌株。在测试的化合物中，发现 7b、7c、7i 和 7j 对革兰氏阳性菌（金黄色葡萄球菌和化脓性链球菌）具有活性，最小抑菌浓度 (MIC) 值在 6.25–25 µg/mL 范围内，并且一些化合物还针对耐甲氧西林金黄色葡萄球菌 (MRSA) 进行了测试。化合物 7c 和 7j 分别在 6.25 和 12.5 µg/mL 的 MIC 值下抑制 MRSA 的生长。还讨论了亲脂性 (C log P) 对所制备产品的生物特征 (MIC) 的影响。从构效关系研究的角度来看，据观察，这些化合物的亲脂特性对其抗菌活性至关重要。此外，对人宫颈癌细胞系 (HeLa) 和小鼠胚胎成纤维细胞系 (NIH 3T3) 的 MTT 细胞毒性研究结果表明，化合物
• Dicationic Ionic Liquid Mediated Synthesis of 5-Arylidine-2,4-thiazolidinediones
  作者：Dhanaji V. Jawale、Umesh R. Pratap、Dinesh L. Lingampalle、Ramrao A. Mane

  DOI：10.1002/cjoc.201190192

  日期：2011.5

  AbstractAn efficient synthesis of 5‐arylidine‐2,4‐thiazolidinediones has been developed using dicationic ionic liquid as green medium and catalyst. This method performed well for the condensation of both aryl as well as heteryl aldehydes with 2,4‐thiazolidinedione and gave 5‐arylidine‐2,4‐thiazolidinediones with excellent yields.
• Synthesis and biological evaluation of novel pyrazolyl-2,4-thiazolidinediones as anti-inflammatory and neuroprotective agents
  作者：Amal M. Youssef、M. Sydney White、Erika B. Villanueva、Ibrahim M. El-Ashmawy、Andis Klegeris

  DOI：10.1016/j.bmc.2010.01.021

  日期：2010.3

  Novel pyrazolyl-2,4-thiazolidinediones were prepared via the reaction of appropriate pyrazolecarboxaldehydes with 2,4-thiazolidinediones and substituted benzyl-2,4-thiazolidinediones. The resultant compounds were first evaluated for their anti-inflammatory and neuroprotective properties in vitro. The active compounds were further studied in vivo by using the formalin-induced paw edema and the turpentine oil-induced granuloma pouch bioassays. We identified four novel compounds that showed protective effects in vitro at non-toxic concentrations, and were also effective in the animal models of acute and sub-acute inflammation. (C) 2010 Elsevier Ltd. All rights reserved.
• A New 4-Thiazolidinone Derivative (Les-6490) as a Gut Microbiota Modulator: Antimicrobial and Prebiotic Perspectives
  作者：Yulian Konechnyi、Tetyana Rumynska、Ihor Yushyn、Serhii Holota、Vira Turkina、Mariana Ryviuk Rydel、Alicja Sękowska、Yuriy Salyha、Olena Korniychuk、Roman Lesyk

  DOI：10.3390/antibiotics13040291

  日期：——

  A novel 4-thiazolidinone derivative Les-6490 (pyrazol-4-thiazolidinone hybrid) was designed, synthesized, and characterized by spectral data. The compound was screened for its antimicrobial activity against some pathogenic bacteria and fungi and showed activity against Staphylococcus and Saccharomyces cerevisiae (the Minimum Inhibitory Concentration (MIC) 820 μM). The compound was studied in the rat adjuvant arthritis model (Freund’s Adjuvant) in vivo. Parietal and fecal microbial composition using 16S rRNA metagenome sequences was checked. We employed a range of analytical techniques, including Taxonomic Profiling (Taxa Analysis), Diversity Metrics (Alpha and Beta Diversity Analysis), Multivariate Statistical Methods (Principal Coordinates Analysis, Principal Component Analysis, Non-Metric Multidimensional Scaling), Clustering Analysis (Unweighted Pair-group Method with Arithmetic Mean), and Comparative Statistical Approaches (Community Differences Analysis, Between Group Variation Analysis, Metastat Analysis). The compound significantly impacted an increasing level of anti-inflammatory microorganisms (Blautia, Faecalibacterium prausnitzii, Succivibrionaceae, and Coriobacteriales) relative recovery of fecal microbiota composition. Anti-Treponemal activity in vivo was also noted. The tested compound Les-6490 has potential prebiotic activity with an indirect anti-inflammatory effect.