3-mercaptotriazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-mercaptotriazole
• 英文别名: (1H-1,2,3-triazol-4-yl)thiol；Triazole sulfide；1-sulfanyltriazole
• 化学式: C₂H₃N₃S
• 分子量: 101.132
• InChiKey: MACMNSLOLFMQKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-mercaptotriazole 、 1,3-dimethyl-9-(oxiran-2-ylmethyl)-3,9-dihydro-1H-purine-2,6-dione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以24.1%的产率得到9-(3-((1H-1,2,4-triazol-3-yl)thio)-2-hydroxypropyl)-1,3-dimethyl 3,9-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  潜在的抗菌乙醇桥连嘌呤唑杂合物作为 MRSA 的双重靶向抑制剂

  摘要：

  开发了一类新的抗菌乙醇桥连嘌呤唑杂化物作为潜在的双靶向抑制剂。生物活性评估表明，部分目标化合物对受试细菌具有显着的抗菌活性，尤其是甲硝唑杂合体3a对MRSA具有显着的抑制活性（MIC = 6 μM），对正常哺乳动物细胞无明显毒性（RAW 264.7）。此外，化合物3a也没有明显诱导MRSA的耐药性，即使经过15次传代。分子模型研究表明，高活性分子3a可以通过氢键插入拓扑异构酶 IA-DNA 和拓扑异构酶 IV-DNA 的碱基对。此外，对抗菌机制的初步研究表明，活性分子3a可以破坏MRSA的细菌膜并插入MRSA DNA中阻止其复制，因此可能表现出很强的抗菌活性。这些结果有力地表明，高活性杂交体3a可用作 MRSA 的潜在双靶向抑制剂，用于进一步开发有价值的抗菌剂。

  DOI：

  10.1016/j.bioorg.2021.105096

文献信息

• Design of a pillar-layered metal-organic framework as high-performance fluorescence sensor for nitroaromatic compounds
  作者：Hai-Tao Wu、Hai-Peng Li、Shu-Ni Li、Yu-Cheng Jiang、Man-Cheng Hu、Quan-Guo Zhai

  DOI：10.1016/j.jssc.2019.121166

  日期：2020.3

  A ternary luminescent cadmium-triazolate-carboxylate framework, L(CH3)(2)NH2][Cd(1245-BTC)(0.5)(3S-TRZ)] (SNNU-111, 1245-BTC = 1245-benzenetetra- carboxylic acid, 3S-TRZ = 3-mercaptotriazole) was successfully designed in this work. X-ray single crystal diffraction results show that Cd atoms are connected by 3S-TRZ ligands to form 2D wave-like layers, which are further extended by 1245-BTC linkers to generate the 3D pillar-layered architecture of SNNU-111. Solid-state and solution photoluminescence both showed that the emissions of SNNU-111 was ascribed to the intraligand charge transfer in 1245-BTC. Benefited from this process, SNNU-111 MOF can act as excellent fluorescence sensor to quantitatively detect involved nitroaromatics including nitrobenzene (NB), 1,2-dinitrobenzene (1,2-DNB), 1,3-dinitrobenzene (1,3-DNB), 2,4-dinitrotoluene (DNT), 2,4,6trinitrotoluene (TNT), and 2,4,6-trinitrophenol (PA) through the fluorescence quenching. The corresponding quenching coefficient (K-sv) values are of 1.0 x 10(4)-1.7 x 10(4)M(-1), which surpass the performance of many reported sensors. Specially, the K-sv value of 1.2 x 10(4)M(-1) for NB is nearly the highest one among all MOF sensors up to now. On the other hand, SNNU-111 sensor also exhibits good sensitivity to nitroaromatics with the detection limits as low as 1.61-5.77 ppm. Overall, the definite pillar-layered structure, fast response and high sensitivity make SNNU-111 a promising fluorescent sensor to detect nitroaromatic compounds.
• Potential antibacterial ethanol-bridged purine azole hybrids as dual-targeting inhibitors of MRSA
  作者：Yuanyuan Hu、Shunyou Hu、Guangxing Pan、Dong Wu、Tiansheng Wang、Congwei Yu、Mohammad Fawad Ansari、Rammohan R. Yadav Bheemanaboina、Yu Cheng、Ligang Bai、Chenghe Zhou、Jiaheng Zhang

  DOI：10.1016/j.bioorg.2021.105096

  日期：2021.9

  A new class of antibacterial ethanol-bridged purine azole hybrids as potential dual-targeting inhibitors was developed. Bioactivity evaluation showed that some of the target compounds had prominent antibacterial activity against the tested bacteria, notably, metronidazole hybrid 3a displayed significant inhibitory activity against MRSA (MIC = 6 μM), and had no obvious toxicity on normal mammalian cells

  开发了一类新的抗菌乙醇桥连嘌呤唑杂化物作为潜在的双靶向抑制剂。生物活性评估表明，部分目标化合物对受试细菌具有显着的抗菌活性，尤其是甲硝唑杂合体3a对MRSA具有显着的抑制活性（MIC = 6 μM），对正常哺乳动物细胞无明显毒性（RAW 264.7）。此外，化合物3a也没有明显诱导MRSA的耐药性，即使经过15次传代。分子模型研究表明，高活性分子3a可以通过氢键插入拓扑异构酶 IA-DNA 和拓扑异构酶 IV-DNA 的碱基对。此外，对抗菌机制的初步研究表明，活性分子3a可以破坏MRSA的细菌膜并插入MRSA DNA中阻止其复制，因此可能表现出很强的抗菌活性。这些结果有力地表明，高活性杂交体3a可用作 MRSA 的潜在双靶向抑制剂，用于进一步开发有价值的抗菌剂。