4-amino-3-(2-fluorobenzyl)-1H-1,2,4-triazole-5(4H)-thione | 554436-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-3-(2-fluorobenzyl)-1H-1,2,4-triazole-5(4H)-thione
• 英文别名: 4-amino-5-[(2-fluorophenyl)methyl]-4H-1,2,4-triazole-3-thiol；4-amino-3-[(2-fluorophenyl)methyl]-1H-1,2,4-triazole-5-thione
• CAS: 554436-95-2
• 化学式: C₉H₉FN₄S
• mdl: MFCD03987287
• 分子量: 224.262
• InChiKey: KRWQCLHYHCMFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异烟酸 、 4-amino-3-(2-fluorobenzyl)-1H-1,2,4-triazole-5(4H)-thione 在 三氯氧磷 作用下， 以78%的产率得到3-(2-fluorobenzyl)-6-(pyridin-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Some Pyridyl- and Thiophenyl-Substituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives as Potent Antibacterial

  摘要：

  在氧氯化磷存在下，4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮 5a-f 与各种芳香族羧酸缩合，合成了目标化合物 6-11a-e。通过红外光谱、$^1H$核磁共振、$^{13}C$核磁共振、元素分析和质谱研究对新合成化合物的结构进行了表征。对所有合成化合物进行了抗菌活性筛选。与参考药物环丙沙星相比，几乎所有被测化合物都对四种不同的细菌菌株具有很强的抗菌活性。与标准药物相比，化合物 6c、6e、8d、9b、9e、11a 和 11b 对所有四种受测细菌菌株的 MIC 值几乎相等或更低，但其余化合物则表现出极佳的抗菌活性。

  DOI：

  10.5012/bkcs.2012.33.12.4180
• 作为产物：
  描述：

  甲基2-氟苯乙酸 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 4-amino-3-(2-fluorobenzyl)-1H-1,2,4-triazole-5(4H)-thione
  参考文献：
  名称：

  一些新型3,6-二取代1,2,4-三唑并[3,4-b]1,3,4-噻二唑衍生物的合成及生物活性

  摘要：

  一系列芳族酰肼 3a-j 是通过将酯 2a-j 与水合肼在甲醇中回流制备的，它们是通过酯化 1a-j 制备的。乙酰肼 3a-j 在用二硫化碳和甲醇氢氧化钾处理后产生二硫代氨基甲酸钾盐 4a-j，在与水合肼一起回流时产生取代的 4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮5a-j。目标化合物 6a-j 通过在多磷酸存在下在回流下缩合呋喃-3-羧酸来合成。通过IR、1 H NMR、13 C NMR、元素分析和质谱研究对新合成化合物的结构进行了表征。筛选所有合成的化合物的脲酶、乙酰胆碱酯酶抑制、抗氧化和碱性磷酸酶抑制活性。几乎所有的化合物 6a-j 对脲酶和乙酰胆碱酯酶的活性均优于参考药物。化合物 6f 和 6g 是比参考没食子酸正丙酯更有效的自由基清除剂。与参考 KH2PO4 相比，化合物 6b 和 6h 显示出优异的碱性磷酸酶活性。

  DOI：

  10.5012/bkcs.2012.33.12.3943

文献信息

• Synthesis, structural elucidation and bioevaluation of 4-amino-1,2,4-triazole-3-thione’s Schiff base derivatives
  作者：Muhammad Rafiq、Muhammad Saleem、Muhammad Hanif、Sung Kwon Kang、Sung-Yum Seo、Ki Hwan Lee

  DOI：10.1007/s12272-015-0688-2

  日期：2016.2

  In this study, a series of ten triazole Schiff base derivatives 6a–j were synthesized through microwave assisted imine formation by reacting substituted amino triazole 5 with different substituted aldehydes. All the synthesized compounds were evaluated for their inhibitory activity against mushroom tyrosinase. Two of the compounds 6a and 6b among the series 6a–j were found to be highly potent tyrosinase inhibitors with IC50 values of 10.09 ± 1.03 and 6.23 ± 0.85 µM, respectively, which were even higher than that of the reference inhibitor kojic acid (IC50 = 16.6 ± 2.8 µM). Compounds 6e and 6f with IC50 values of 20.27 ± 2.78 and 26.02 ± 4.14 µM, respectively, were comparable to the reference inhibitor, and the remaining compounds had a moderate inhibitory activity against mushroom tyrosinase. The most potent compounds (6a, 6b) were used in the kinetic and optical analyses. The inhibition kinetics analyzed with Lineweaver–Burk plots revealed that both compounds 6a and 6b were non-competitive inhibitors of tyrosinase with inhibition constant values of 0.023 and 0.022 mM, respectively.

  在本研究中，通过微波辅助的亚胺形成合成了一系列十种三氮唑希夫碱衍生物6a–j，这些衍生物是通过将取代氨基三氮唑5与不同取代醛反应而得到的。所有合成的化合物对蘑菇酪氨酸酶的抑制活性进行了评估。在6a–j系列中，化合物6a和6b被发现是高度有效的酪氨酸酶抑制剂，IC50值分别为10.09 ± 1.03和6.23 ± 0.85 µM，甚至高于参考抑制剂曲酸（IC50 = 16.6 ± 2.8 µM）。化合物6e和6f的IC50值分别为20.27 ± 2.78和26.02 ± 4.14 µM，表现出与参考抑制剂相当的抑制活性，其余化合物对蘑菇酪氨酸酶具有中等抑制活性。最有效的化合物（6a，6b）被用于动力学和光学分析。通过Lineweaver–Burk图分析的抑制动力学显示，化合物6a和6b都是酪氨酸酶的非竞争性抑制剂，抑制常数值分别为0.023和0.022 mM。
• Synthesis and Biological Activities of Some New 3,6-Disubstituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives
  作者：Muhammad Rafiq、Muhammad Saleem、Muhammad Hanif、Muhammad Rizwan Maqsood、Nasim Hasan Rama、Ki-Hwan Lee、Sung-Yum Seo

  DOI：10.5012/bkcs.2012.33.12.3943

  日期：2012.12.20

  inhibition, antioxidant and alkaline phosphatase inhibition activity. Almost all of the compounds 6a-j showed good to excellent activities against urease and acetylcholine esterase more than the reference drugs. Compounds 6f and 6g were more potent scavenger of free radicals than the reference n-propyl gallate. Compound 6b and 6h showed excellent activities of alkaline phosphatase as compare to the reference

  一系列芳族酰肼 3a-j 是通过将酯 2a-j 与水合肼在甲醇中回流制备的，它们是通过酯化 1a-j 制备的。乙酰肼 3a-j 在用二硫化碳和甲醇氢氧化钾处理后产生二硫代氨基甲酸钾盐 4a-j，在与水合肼一起回流时产生取代的 4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮5a-j。目标化合物 6a-j 通过在多磷酸存在下在回流下缩合呋喃-3-羧酸来合成。通过IR、1 H NMR、13 C NMR、元素分析和质谱研究对新合成化合物的结构进行了表征。筛选所有合成的化合物的脲酶、乙酰胆碱酯酶抑制、抗氧化和碱性磷酸酶抑制活性。几乎所有的化合物 6a-j 对脲酶和乙酰胆碱酯酶的活性均优于参考药物。化合物 6f 和 6g 是比参考没食子酸正丙酯更有效的自由基清除剂。与参考 KH2PO4 相比，化合物 6b 和 6h 显示出优异的碱性磷酸酶活性。
• Acetylcholinesterase inhibition activity of some quinolinyl substituted triazolothiadiazole derivatives
  作者：Muhammad Rafiq、Muhammad Saleem、Muhammad Hanif、Qamar Abbas、Ki Hwan Lee、Sung-Yum Seo

  DOI：10.1134/s1068162015020089

  日期：2015.3

  A series of aralkanoic acids was converted into aralkanoic acid hydrazides through their esters formation. The aralkanoic acid hydrazides upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazinate salts, which on refluxing with aqueous hydrazine hydrate yielded 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles. The target compounds, 3-aralkyl-6-(substitutedquinolinyl) [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles, were synthesized by condensing various quinolinyl substituted carboxylic acids with 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles in phosphorus oxychloride. The structures of the newly synthesized triazolothiadiazoles were characterized by IR, H-1 NMR, C-13 NMR, and elemental analysis studies. The structure of one of the 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles was unambiguously deduced by single crystal X-ray diffraction analysis. All the synthesized compounds were screened for their acetylcholinesterase inhibition activities. Four of the triazolothiadiazoles exhibited excellent acetylcholinesterase inhibition activities as compared to the reference inhibitor.
• Some Pyridyl- and Thiophenyl-Substituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives as Potent Antibacterial
  作者：Muhammad Rizwan Maqsood、Muhammad Hanif、Muhammad Rafiq、Muhammad Saleem、Sumera Zaib、Aftab Ahmed Khan、Mazhar Iqbal、Jamshed Iqbal、Nasim Hasan Rama、Sung-Yum Seo、Ki-Hwan Lee

  DOI：10.5012/bkcs.2012.33.12.4180

  日期：2012.12.20

  The target compounds 6-11a-e were synthesized by condensing 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-f with various aromatic carboxylic acids in the presence of phosphorous oxychloride. The structures of newly synthesized compounds were characterized by IR, $^1H$ NMR, $^13}C$ NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their antibacterial activity. Almost all the tested compounds were potent against four different strains of bacteria when compared with that of reference drug ciprofloxacin. Compounds 6c, 6e, 8d, 9b, 9e, 11a and 11b showed nearly equal or lower MIC values than standard drug, against all four tested bacterial strains but rest of the compounds showed excellent antibacterial activities.

  在氧氯化磷存在下，4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮 5a-f 与各种芳香族羧酸缩合，合成了目标化合物 6-11a-e。通过红外光谱、$^1H$核磁共振、$^13}C$核磁共振、元素分析和质谱研究对新合成化合物的结构进行了表征。对所有合成化合物进行了抗菌活性筛选。与参考药物环丙沙星相比，几乎所有被测化合物都对四种不同的细菌菌株具有很强的抗菌活性。与标准药物相比，化合物 6c、6e、8d、9b、9e、11a 和 11b 对所有四种受测细菌菌株的 MIC 值几乎相等或更低，但其余化合物则表现出极佳的抗菌活性。