4-(4-methylphenyl)-3-(2-methylfuran-3-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione | 1246010-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-methylphenyl)-3-(2-methylfuran-3-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione
• 英文别名: 3-(2-methylfuran-3-yl)-4-(4-methylphenyl)-1H-1,2,4-triazole-5-thione
• CAS: 1246010-99-0
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: VHTIGGRETOROON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-methylphenyl)-3-(2-methylfuran-3-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione 、 2-溴-N-(2-硝基苯基)乙酰胺 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 N-(2-nitrophenyl)-2-((4-(4-methylphenyl)-5-(2-methylfuran-3-yl)-4H-1,2,4-triazol-3-yl)-sulfanyl)acetamide
  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 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 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

文献信息

• 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.
• A Search for Dual Action HIV-1 Reverse Transcriptase, Bacterial RNA Polymerase Inhibitors
  作者：Agata Paneth、Tomasz Frączek、Agnieszka Grzegorczyk、Dominika Janowska、Anna Malm、Piotr Paneth

  DOI：10.3390/molecules22111808

  日期：——

  Using molecular modeling approach, potential antibacterial agents with triazole core were proposed. A moderate to weak level of antibacterial activity in most of the compounds have been observed, with best minimal inhibitory concentration (MIC) value of 0.003 mg/mL, as shown by the 15 against S. epidermidis. Studied compounds were also submitted to the antifungal assay. The best antifungal activity

  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。