2-(2-methyl-3-furoyl)-N-(2-methylphenyl)hydrazinecarbothioamide | 438232-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2-(2-methyl-3-furoyl)-N-(2-methylphenyl)hydrazinecarbothioamide
• 英文别名: 1-[(2-methylfuran-3-carbonyl)amino]-3-(2-methylphenyl)thiourea
• CAS: 438232-76-9
• 化学式: C₁₄H₁₅N₃O₂S
• 分子量: 289.358
• InChiKey: CXHWRSFABRDKCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-3-furoyl)-N-(2-methylphenyl)hydrazinecarbothioamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-(2-methylfuran-3-yl)-4-(2-methylphenyl)-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  Antimicrobial Properties of 4-Aryl-3-(2-methyl-furan-3-yl)-Δ²-1,2,4-triazoline-5-thiones

  摘要：

  Four 4-aryl-3-(2-methyl-furan-3-yl)-Delta(2)-1,2,4-triazole-5-thiones were synthesized by intramolecular cyclization of 4-aryl-1-[(2-methyl-furan-3-yl)carbonyl]thiosemicarbazides in alkaline medium. The antimicrobial activity of the synthesized triazoles was evaluated. Semiempirical calculations of geometries, energies, and QSAR parameters have been determined in the hope of gaining insight into different biological activities of closely related isomers. New RM1 parameterization has been shown to perform very well for this class of compounds.

  DOI：

  10.1080/10426500802705297
• 作为产物：
  描述：

  2-甲基呋喃-3-羧肼 、 邻甲苯异硫氰酸酯 以 乙醇 为溶剂， 反应 0.5h， 生成 2-(2-methyl-3-furoyl)-N-(2-methylphenyl)hydrazinecarbothioamide
  参考文献：
  名称：

  1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation

  摘要：

  研究人员合成了一系列 N1 位被 5 元杂芳基环取代的 4-芳基硫代氨基甲酸盐，并在体外评估了它们对淋球菌增殖的抑制作用和对宿主细胞的细胞毒性。在对宿主细胞无毒的浓度下，与磺胺嘧啶相比，所有研究化合物都显示出了极佳的抗寄生虫效果，这表明它们的抗淋球菌活性具有很高的选择性。通过 DFT 计算研究的生物活性差异表明，4-芳基-硫代氨基甲酸盐对淋球菌增殖的抑制活性与分子的电子结构有关。此外，这些化合物还被测试为潜在的抗菌剂。即使在高浓度下，也没有观察到所有化合物对任何受试微生物有抑制生长的作用。

  DOI：

  10.3390/molecules19079926

文献信息

• 1,4-Disubstituted Thiosemicarbazide Derivatives are Potent Inhibitors of Toxoplasma gondii Proliferation
  作者：Katarzyna Dzitko、Agata Paneth、Tomasz Plech、Jakub Pawełczyk、Paweł Stączek、Joanna Stefańska、Piotr Paneth

  DOI：10.3390/molecules19079926

  日期：——

  A series of 4-arylthiosemicarbazides substituted at the N1 position with a 5-membered heteroaryl ring was synthesized and evaluated in vitro for T. gondii inhibition proliferation and host cell cytotoxicity. At non-toxic concentrations for the host cells all studied compounds displayed excellent anti-parasitic effects when compared to sulfadiazine, indicating a high selectivity of their anti-T. gondii activity. The differences in bioactivity investigated by DFT calculations suggest that the inhibitory activity of 4-aryl-thiosemicarbazides towards T. gondii proliferation is connected with the electronic structure of the molecule. Further, these compounds were tested as potential antibacterial agents. No growth-inhibiting effect on any of the test microorganisms was observed for all the compounds, even at high concentrations.

  研究人员合成了一系列 N1 位被 5 元杂芳基环取代的 4-芳基硫代氨基甲酸盐，并在体外评估了它们对淋球菌增殖的抑制作用和对宿主细胞的细胞毒性。在对宿主细胞无毒的浓度下，与磺胺嘧啶相比，所有研究化合物都显示出了极佳的抗寄生虫效果，这表明它们的抗淋球菌活性具有很高的选择性。通过 DFT 计算研究的生物活性差异表明，4-芳基-硫代氨基甲酸盐对淋球菌增殖的抑制活性与分子的电子结构有关。此外，这些化合物还被测试为潜在的抗菌剂。即使在高浓度下，也没有观察到所有化合物对任何受试微生物有抑制生长的作用。
• Antimicrobial Properties of 4-Aryl-3-(2-methyl-furan-3-yl)-Δ²-1,2,4-triazoline-5-thiones
  作者：Agata Siwek、Monika Wujec、Joanna Stefańska、Piotr Paneth

  DOI：10.1080/10426500802705297

  日期：2009.11.24

  Four 4-aryl-3-(2-methyl-furan-3-yl)-Delta(2)-1,2,4-triazole-5-thiones were synthesized by intramolecular cyclization of 4-aryl-1-[(2-methyl-furan-3-yl)carbonyl]thiosemicarbazides in alkaline medium. The antimicrobial activity of the synthesized triazoles was evaluated. Semiempirical calculations of geometries, energies, and QSAR parameters have been determined in the hope of gaining insight into different biological activities of closely related isomers. New RM1 parameterization has been shown to perform very well for this class of compounds.