5-ethoxymethylene-2-thioxo-thiazolidin-4-one | 86240-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-ethoxymethylene-2-thioxo-thiazolidin-4-one
• 英文别名: Ethoxymethylenerhodanine；5-(ethoxymethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 86240-28-0
• 化学式: C₆H₇NO₂S₂
• mdl: MFCD00175004
• 分子量: 189.259
• InChiKey: BPNCBJFIFVKUAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxymethylene-2-thioxo-thiazolidin-4-one 在 hydrazine hydrate 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以75%的产率得到5-hydrazinylmethylene-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Facile Synthesis of Some New Pyrazole-Based 2-Thioxo-4-thiazolidinone

  摘要：

  5-Ethoxymethylene-2-thioxo-4-thiazolidinone (1) reacts with hydrazine hydrate at room temperature to afford 5-(hydrazinylmethylene)-2-thioxo-4-thiazolidinone (3). Compound 3 condensed with different aromatic aldehydes 6a-d in ethanol in the presence of a few drops of piperidine to give the corresponding Schiff's bases 7a-d. On the other hand, compound 3 reacts with o-hydroxybenzaldehyde derivatives 8a and 8b in refluxing ethanol catalyzed by a few drops of piperidine to yield 1H-inadzolyl-2-thioxo-4-thiazolidinones 9a and 9b. Reaction of compound 3 with -ketoesters 10a and 10b or -diketones 10c-e in refluxing glacial acetic acid furnished the pyrazolyl-2-thioxo-4-thiazolidinone derivatives 11a-e. Also, compound 3 reacts with some different enaminones 12a-f in refluxing glacial acetic acid to afford the new pyrazolyl-2-thioxo-4-thiazolidinone derivatives 13a-f. Pyrazoles 15a-d was obtained via reaction of compound 3 with chalcones 14a-d in dimethylformamide (DMF). The structures of all the newly synthesized products were confirmed on the basis of their elemental and spectral data, and a plausible mechanism has been postulated to account for their formation.

  DOI：

  10.1080/00397911.2015.1100312
• 作为产物：
  描述：

  罗丹宁 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 2.0h， 生成 5-ethoxymethylene-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  新型噻唑烷酮-双氯芬酸杂化分子的合成及生物活性评价

  摘要：

  摘要 设计并合成了一系列新型[2-(2,6-二氯苯基氨基)-苯基]-乙酸N`-3-(取代)-4-噻唑烷-5-亚基甲基-酰肼衍生物。合成化合物的结构由其 1H NMR、13C NMR 和 LCMS 光谱数据证实。根据美国 NCI 协议筛选目标化合物的体外抗癌活性、对布氏锥虫 (Tbb) 的体外杀锥虫活性，并评估对大鼠角叉菜胶水肿模型的抗炎活性。生物筛选数据导致鉴定了化合物 3.3（[2-(2,6-二氯-苯基氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-hydrazide）和3.7 ([2-(2, 6-二氯-苯氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-3-(3-trifluoromethylphenyl)thiazolidin-5-ylidenemethyl)-hydrazide) -细胞肺癌 NCI-H522

  DOI：

  10.1080/10426507.2020.1759060

文献信息

• 5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells
  作者：Julia Senkiv、Nataliya Finiuk、Danylo Kaminskyy、Dmytro Havrylyuk、Magdalena Wojtyra、Iryna Kril、Andrzej Gzella、Rostyslav Stoika、Roman Lesyk

  DOI：10.1016/j.ejmech.2016.03.089

  日期：2016.7

  structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic action was confirmed. 5-[5-(2-Hydroxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one (compound 1) was selected as most active agent against HL-60 and HL-60/ADR

  本文介绍了以烯胺基连接吡唑核心的5-ene-4-thiazolidinone衍生物的合成方法。化合物的结构和纯度通过包括X射线分析在内的分析和光谱数据进行了确认。筛选目标化合物的抗癌活性，并确认了选择性抗白血病作用。选择5- [5-（2-羟基苯基）-3-苯基-4,5-二氢吡唑-1-基亚甲基] -3-（3-乙酰氧基苯基）-2-硫代噻唑烷-4-（化合物1）作为最有效的化合物抗HL-60和HL-60 / ADR细胞系的药物; IC 50  = 118 nM / HL-60，对伪正常细胞毒性低。线粒体依赖性细胞凋亡被认为是1作用的主要模式。另外，化合物的作用诱发了G 0 / G 1。 抑制所处理的细胞并引起细胞分裂的抑制，并且与ROS产生的活化有关。
• Exploring rhodanine linked enamine–carbohydrazide derivatives as mycobacterial carbonic anhydrase inhibitors: Design, synthesis, biological evaluation, and molecular docking studies
  作者：Sarvan Maddipatla、Bulti Bakchi、Rutuja Rama Gadhave、Andrea Ammara、Shashikanta Sau、Bandela Rani、Srinivas Nanduri、Nitin Pal Kalia、Claudiu T. Supuran、Venkata Madhavi Yaddanapudi

  DOI：10.1002/ardp.202400064

  日期：2024.7

  exploring their potential as inhibitors of mycobacterial carbonic anhydrase. The findings reveal their efficacy, displaying notable selectivity toward the mycobacterial carbonic anhydrase 2 (mtCA 2) enzyme. While exhibiting moderate activity against human carbonic anhydrase isoforms, this series demonstrates promising selectivity, positioning these compounds as potential antitubercular agents. Compound 6d

  随着耐多药结核病的兴起，寻找一种结合新作用机制的替代性优质治疗方案变得至关重要。为了实现这一目标，我们开发并合成了一系列新的绕丹宁连接的烯胺碳酰肼衍生物，探索它们作为分枝杆菌碳酸酐酶抑制剂的潜力。研究结果揭示了它们的功效，对分枝杆菌碳酸酐酶 2 (mtCA 2) 酶表现出显着的选择性。该系列化合物虽然对人碳酸酐酶异构体表现出中等活性，但表现出良好的选择性，将这些化合物定位为潜在的抗结核药物。化合物6d是该系列中最好的一种，对 mtCA 2 的K i值为 9.5 µM。大多数化合物对 Mtb H37Rv 菌株表现出中等至良好的抑制作用；化合物11k的最低抑制浓度为 1 µg/mL。分子对接研究表明，化合物6d和11k显示出与锌离子的金属配位，就像经典的 CA 抑制剂一样。
• Kempter,G. et al., Chemische Berichte, 1965, vol. 98, p. 955 - 961
  作者：Kempter,G. et al.

  DOI：——

  日期：——
• Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Karpenko、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.ejmech.2014.07.103

  日期：2014.10

  A series of novel 4-thiazolidinone-pyrazoline conjugates have been synthesized and tested for anti-Trypanosoma brucei activity. Screening data allowed us to identify five thiazolidinone-pyrazoline hybrids, which possess promising trypanocidal activity, with IC50 <= 1.2 mu M. The highest active thiazolidinone-pyrazoline conjugates 3c and 6b (IC50 values of 0.6 mu M and 0.7 mu M, respectively) were 6-times more potent antitrypanosomal agents than nifurtimox. In addition, these compounds, as well as 6d and 6e had selectivity index higher than 50, and were more selective than nifurtimox. SAR study included substituent variations at the pyrazoline moiety, modifications of N3 position of the thiazolidinone portion, elongation of the linker between the heterocycles, as well as rhodanine-isorhodanine isomerism. It was also shown that methyl or aryl substitution at the thiazolidinone N3-position is crucial for trypanocidal activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Das,B. et al., Journal of the Indian Chemical Society, 1960, vol. 37, # 10, p. 603 - 610
  作者：Das,B. et al.

  DOI：——

  日期：——