4,5-二苯基-4H-1,2,4-噻唑-3-硫醇 | 38942-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5-二苯基-4H-1,2,4-噻唑-3-硫醇
• 英文名称: cyclohexyl-4 phenyl-5 dihydro-2,4 triazole-1,2,4 thione-3
• 英文别名: 4-cyclohexyl-5-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione；4-cyclohexyl-5-phenyl-4H-1,2,4-triazole-3-thiol；4-cyclohexyl-3-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 38942-57-3
• 化学式: C₁₄H₁₇N₃S
• mdl: MFCD01408815
• 分子量: 259.375
• InChiKey: VTLLUDFHDJESNU-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C(Solv: ligroine (8032-32-4))
• 沸点：
  365.0±25.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  4,5-二苯基-4H-1,2,4-噻唑-3-硫醇 在 氢氧化钾 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 1-[4-[(4-Cyclohexyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]but-2-ynyl]azepane
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 3-(4-tert-amino-2-butynyl)thio and alkyl/alkenylthio-4,5-disubstituted-4H-1,2,4-triazoles

  摘要：

  DOI：

  10.1016/0223-5234(91)90035-l
• 作为产物：
  描述：

  环己基异硫氰酸脂 在 sodium hydroxide 作用下， 生成 4,5-二苯基-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  4,5-二取代-1,2,4-三唑硫代乙酸酯衍生物的合成，抗炎，抗菌潜力和分子对接研究

  摘要：

  背景：在本研究中，进行了九种新的[（4,5-二取代-4H-1,2,4-三唑-3-基）硫烷基]乙酸乙基酯衍生物2（ai）的合成和生物学评估。 方法：通过分析和光谱数据表征标题化合物。使用角叉菜胶诱导的大鼠爪水肿方法筛选所有合成的化合物的体内抗炎活性和体外抗菌活性。所有化合物均表现出良好的抗炎活性。尤其是化合物2h产生了最大的效果，即与标准双氯芬酸相当，为62.5％。抗菌筛选结果表明，一些新合成的化合物表现出良好的抗菌活性，尤其是对大肠杆菌。 结果：通过对接分析，还研究了所有合成的三唑的硫代乙酸酯衍生物与炎症途径的两个重要靶标酶COX-I和COX-II的相互作用。所有化合物对两种酶均显示出良好的结合亲和力，对COX-1的2e kcal / mol的最大值为-8.1。 结论：对接分析预测我们的化合物与其他非活性NSAIDS一样，通过抑制炎症途径的COX-I和COX-II来非选择性地减轻炎症。

  DOI：

  10.2174/1570180815666180810122226

文献信息

• Quinazolinones, 13.Comm. Synthesis of 3-[2-(2,3-Dihydro-5-phenyl-4-substituted-3H-1,2,4-triazole-3-thione-2-yl)-acetylamino]-2-methyl-4(3H)-quinazolinones and their pharmacological activities
  作者：Servet Büyüktimkin、Nadir Büyüktimkin、Osman Özdemir、Sevim Rollas

  DOI：10.1002/ardp.19893220112

  日期：——

  Some 2‐methyl‐3‐triazole‐substituted‐4(3H)‐quinazolinones 3a–f were prepared and tested for their H1‐ and H2‐ antihistaminic activities. In addition these compounds are central nervous system depressants and anticonvulsants. 3e shows highly significant decrease of locomotor activity.

  制备了一些 2-甲基-3-三唑-取代的-4(3H)-喹唑啉酮3a-f，并测试了它们的H1-和H2-抗组胺活性。此外，这些化合物是中枢神经系统抑制剂和抗惊厥药。图 3e 显示了自发活动的高度显着降低。
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• Malbec, Frederique; Milcent, Rene; Barbier, Geo, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1689 - 1698
  作者：Malbec, Frederique、Milcent, Rene、Barbier, Geo

  DOI：——

  日期：——
• Synthesis and antimicrobial activity of Ni(II), Co(II), Zn(II) and Cd(II) complexes of 4-substituted-3-mercapto-5-phenyl-4H-1,2,4-triazoles
  作者：Z Muhi-Eldeen、K Al-Obaidi、M Nadir、VF Roche

  DOI：10.1016/0223-5234(92)90097-k

  日期：1992.3

  Ni(II), Co(II), Zn(II) and Cd(II) complexes of 3-mercapto-4-phenyl(cyclohexyl)-4H-1,2,4-triazoles were prepared and characterized by elemental analyses and standard spectroscopic techniques. In vitro antimicrobial activity of the complexes was determined against a variety of bacterial (Gram-positive and Gram-negative) and fungal species. While the Ni, Co and Zn complexes exhibited little or no activity against the organisms studied in this work, complexes of both the 4-phenyl 13 and 4-cyclohexyl 12 substituted triazoles were highly active as antifungal agents. Both 12 and 13, while significantly superior to the prototypical antifungal nystatin in inhibiting the growth of Candida albicans and Candida pseudotropicalis, showed equal effectiveness against Saccharomyces cerevisiae. The antibacterial activity of the Cd complexes was better than that observed for any of the other metal complexes, but generally not comparable to that of the reference antibiotic, streptomycin with the exception of the 4-cyclohexyl triazole complex 12, which was equivalent to streptomycin against Staphylococcus aureus and Escherichia coli.
• BUYUKTIMKIN, SERVET;BUYUKTIMKIN, NADIR;OZDEMIR, OSMAN;ROLLAS, SEVIM, ARCH. PHARM., 322,(1989) N, C. 49-51
  作者：BUYUKTIMKIN, SERVET、BUYUKTIMKIN, NADIR、OZDEMIR, OSMAN、ROLLAS, SEVIM

  DOI：——

  日期：——