2-(3-nitro-phenylimino)-thiazolidin-4-one | 33260-39-8

• 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: 2-(3-nitro-phenylimino)-thiazolidin-4-one
• 英文别名: 2-(m-Nitrophenyl)-iminothiazolidin-4-on；2-[(3-nitrophenyl)amino]-1,3-thiazol-4(5H)-one；2-(3-nitrophenyl)imino-1,3-thiazolidin-4-one
• CAS: 33260-39-8
• 化学式: C₉H₇N₃O₃S
• mdl: MFCD03304265
• 分子量: 237.239
• InChiKey: ZOGUWKDWVNVDOL-UHFFFAOYSA-N

物化性质

• 溶解度：
  >35.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 2-(3-nitro-phenylimino)-thiazolidin-4-one 生成 2-chloroacetylimino-3-(3-nitro-phenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Svetkin,Yu.V. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 115 - 116

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯胺 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(3-nitro-phenylimino)-thiazolidin-4-one
  参考文献：
  名称：

  New thiazolidinyl analogs containing pyridine ring: synthesis, biological evaluation and QSAR studies

  摘要：

  A series of pyridine derivatives of thiazolidin-4-ones (4a-4o) has been synthesized. Structures of these compounds were established on the basis of elemental analysis, IR, H-1 NMR, C-13 NMR, and Mass spectral data. All the synthesized compounds have been evaluated for their anti-inflammatory and analgesic effects. The results showed that compound 2-[4-methylphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one (4d), 2-(2,4-dinitro-phenylhydrazinylidine)-5-(1H-pyridin-2-yl-methylidene)-1,3-thiazolidin-4-one (4h), and 2-[3-nitro-phenylimino]-5-(1H-pyridin-2-yl-methylidene)-1,3-thiazolidin-4-one (4j) exhibited good anti-inflammatory and analgesic activity. Compound 4h was found to be the most active compound of the series with an interesting dual anti-inflammatory and analgesic activity. Docking simulation was performed to position synthesized compounds into the active site of COX-2. The relationships of energy-based docking score with analgesic and anti-inflammatory activities were also investigated by linear regression method. The QSAR models with R (2) of 0.621 and 0.740 were developed for analgesic and anti-inflammatory activities, respectively.

  DOI：

  10.1007/s00044-012-0149-0

文献信息

• Design, Synthesis, Cytoselective Toxicity, Structure–Activity Relationships, and Pharmacophore of Thiazolidinone Derivatives Targeting Drug-Resistant Lung Cancer Cells
  作者：Hongyu Zhou、Shuhong Wu、Shumei Zhai、Aifeng Liu、Ying Sun、Rongshi Li、Ying Zhang、Sean Ekins、Peter W. Swaan、Bingliang Fang、Bin Zhang、Bing Yan

  DOI：10.1021/jm7012024

  日期：2008.3.13

  identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460 taxR at an IC 50 between 0.21 and 2.93 microM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 microM. Structure-activity relationship studies revealed that

  通过应用迭代文库方法，已从372噻唑烷酮类似物中鉴定出十种细胞选择性化合物。这些化合物在0.250和2.93 microM之间的IC 50选择性杀死了非小细胞肺癌细胞系H460及其抗紫杉醇的变体H460 taxR，同时在高达195 microM的浓度下对正常人成纤维细胞的毒性大大降低。结构-活性关系研究表明：（1）4-噻唑烷酮环（图1中的环B）上的氮原子不能被取代；（2）环A上的多个取代在各个位置都可以容忍；（3）取代环C上的C 1 -C 4基团限于-NMe 2基团。来源于活性分子的药效基团表明，两个氢键受体和三个疏水区是共同的特征。
• Design, Synthesis and Biological Evaluation of Novel Thiazolidinone Derivatives
  作者：Reshma Sathyanarayana、Boja Poojary、B. Sukesh Kumar、Vasantha Kumar、Rajesh P. Shastry、Shamprasad Varija Raghu

  DOI：10.14233/ajchem.2021.23337

  日期：——

  In present study, the novel thiazolidinone derivatives were designed and synthesized. The formation of the target compounds was confirmed by the elemental analyses, FT-IR, mass spectroscopy and 1H NMR spectroscopy. These derivatives were subjected to antibacterial and antioxidant activities. The antibacterial results revealed that these derivatives were selectively active against Gram-negative Pseudomonas aeruginosa bacteria. Also, these derivatives displayed a good DPPH radical scavenging effect. Drosophila melanogaster flies were used for evaluating the toxic impact of novel thiazolidinone derivatives.

  本研究设计并合成了新型噻唑烷酮衍生物。通过元素分析、傅立叶变换红外光谱、质谱和 1H 通过元素分析、傅立叶变换红外光谱、质谱和 1H NMR 光谱证实了目标化合物的形成。这些衍生物具有抗菌和抗氧化活性。抗菌 抗菌结果表明，这些衍生物对革兰氏阴性的 铜绿假单胞菌。此外，这些衍生物还显示出良好的 DPPH 自由基清除效果。 效应。利用黑腹果蝇来评估新型噻唑烷酮 衍生物的毒性影响。