1-[(2-Methylfuran-3-carbonyl)amino]-3-(4-methylphenyl)thiourea | 891085-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 1-[(2-Methylfuran-3-carbonyl)amino]-3-(4-methylphenyl)thiourea
• CAS: 891085-13-5
• 化学式: C₁₄H₁₅N₃O₂S
• 分子量: 289.358
• InChiKey: PDNARXDYQOHIOE-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：

  1-[(2-Methylfuran-3-carbonyl)amino]-3-(4-methylphenyl)thiourea 在 sodium hydroxide 作用下， 反应 2.0h， 生成 4-(4-methylphenyl)-3-(2-methylfuran-3-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  寻找双重作用 HIV-1 逆转录酶、细菌 RNA 聚合酶抑制剂

  摘要：

  使用分子建模方法，提出了具有三唑核的潜在抗菌剂。已观察到大多数化合物具有中等至微弱的抗菌活性，最佳最小抑菌浓度 (MIC) 值为 0.003 mg/mL，如针对表皮葡萄球菌的 15 所示。所研究的化合物也进行了抗真菌试验。对 16 种检测到最佳抗真菌活性，MIC 分别为 0.125 和 0.25 mg/mL，分别对抗白色念珠菌和近平滑念珠菌。

  DOI：

  10.3390/molecules22111808
• 作为产物：
  描述：

  2-甲基呋喃-3-羧肼 、 对甲苯异硫氰酸酯 以 乙醇 为溶剂， 反应 2.0h， 生成 1-[(2-Methylfuran-3-carbonyl)amino]-3-(4-methylphenyl)thiourea
  参考文献：
  名称：

  寻找双重作用 HIV-1 逆转录酶、细菌 RNA 聚合酶抑制剂

  摘要：

  使用分子建模方法，提出了具有三唑核的潜在抗菌剂。已观察到大多数化合物具有中等至微弱的抗菌活性，最佳最小抑菌浓度 (MIC) 值为 0.003 mg/mL，如针对表皮葡萄球菌的 15 所示。所研究的化合物也进行了抗真菌试验。对 16 种检测到最佳抗真菌活性，MIC 分别为 0.125 和 0.25 mg/mL，分别对抗白色念珠菌和近平滑念珠菌。

  DOI：

  10.3390/molecules22111808

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。
• Searching for novel scaffold of triazole non-nucleoside inhibitors of HIV-1 reverse transcriptase
  作者：Tomasz Frączek、Agata Paneth、Rafał Kamiński、Agnieszka Krakowiak、Piotr Paneth

  DOI：10.3109/14756366.2015.1039531

  日期：——

  Azoles are a promising class of the new generation of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). From thousands of reported compounds, many possess the same basic structure of an aryl substituted azole ring linked by a thioglycolamide chain with another aromatic ring. In order to find novel extensions for this basic scaffold, we explored the 5-position substitution pattern of triazole NNRTIs using molecular docking followed by the synthesis of selected compounds. We found that heterocyclic substituents in the 5-position of the triazole ring are detrimental to the inhibitory activity of compounds with four-membered thioglycolamide linker and this substitution seems to be viable only for compounds with shorter two-membered linker. Promising compound, N-(4-carboxy-2-chlorophenyl)-2-((4-benzyl-5-methyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetamide, with potent inhibitory activity and acceptable aqueous solubility has been identified in this study that could serve as lead scaffold for the development of novel water-soluble salts of triazole NNRTIs.
• 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.