methyl [4-oxo-2-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazono]-1,3-thiazolidin-5-ylidene]acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl [4-oxo-2-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazono]-1,3-thiazolidin-5-ylidene]acetate
• 英文别名: methyl 2-[4-oxo-2-[2-(2-oxoindol-3-yl)hydrazinyl]-1,3-thiazol-5-ylidene]acetate
• 化学式: C₁₄H₁₀N₄O₄S
• mdl: MFCD03289676
• 分子量: 330.324
• InChiKey: WITJVXDIERUASA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  109.22
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  靛红 、 氨基硫脲 、 丁炔二酸二甲酯 在 氯乙酸 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以87%的产率得到methyl [4-oxo-2-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazono]-1,3-thiazolidin-5-ylidene]acetate
  参考文献：
  名称：

  Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones

  摘要：

  Three-component reactions of oxindole derivatives, thiosemicarbazide with dialkyl acetylenedicarboxylate (or maleimide) led to novel indole-hydrazono thiazolidinones in high-to-excellent yields. The antioxidant activities of the synthesized compounds were studied by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Among the products, those with amide moiety exhibited better antioxidant activities than other ester derivatives of indole-hydrazono thiazolidinones. Minimum bactericidal concentration (MBC) was evaluated against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) at different concentrations. However, the MBC values for compounds with amide group in their skeleton exhibited higher antibacterial activity than compounds with ester group. Therefore, it is assumed that these compounds could be used as effective antioxidant and antibacterial agents.[GRAPHICS]

  DOI：

  10.1007/s00706-018-2292-x

文献信息

• Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones
  作者：Sakineh Asghari、Maryam Pourshab、Mojtaba Mohseni

  DOI：10.1007/s00706-018-2292-x

  日期：2018.12

  Three-component reactions of oxindole derivatives, thiosemicarbazide with dialkyl acetylenedicarboxylate (or maleimide) led to novel indole-hydrazono thiazolidinones in high-to-excellent yields. The antioxidant activities of the synthesized compounds were studied by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Among the products, those with amide moiety exhibited better antioxidant activities than other ester derivatives of indole-hydrazono thiazolidinones. Minimum bactericidal concentration (MBC) was evaluated against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) at different concentrations. However, the MBC values for compounds with amide group in their skeleton exhibited higher antibacterial activity than compounds with ester group. Therefore, it is assumed that these compounds could be used as effective antioxidant and antibacterial agents.[GRAPHICS]