ethyl 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate | 91759-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate
• 英文别名: ethyl 2-(4,5-diphenyl-4H-1,2,4-triazol-3-ylthio)acetate；ethyl [(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate；3,4-Diphenyl-5-ethoxycarbonylmethylthio-1,2,4-triazol；(4,5-diphenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid ethyl ester；ethyl 2-[(4,5-diphenyl-1,2,4-triazol-3-yl)sulfanyl]acetate
• CAS: 91759-70-5
• 化学式: C₁₈H₁₇N₃O₂S
• 分子量: 339.418
• InChiKey: LOTMEANLMQXAPB-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  525.3±52.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 42.0h， 生成 [3-{[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]methyl}-1-(pyrrolidin-1-ylmethyl)-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]acetic acid
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives

  摘要：

  This study presents the synthesis and spectral analysis of new derivatives of 1,2,4-triazole-3-thione and 1,3,4-thiadiazole. New compounds were prepared by cyclization reaction of acyl thiosemicarbazide derivatives in the presence of alkaline and acidic media. All synthesized compounds were screened for their in vitro antibacterial activity by using the agar dilution technique. Six of the compounds had potential activity against Gram-positive bacteria (minimal inhibitory concentration [MIC] = 15.63-500 mu g/mL). Some compounds showed good activity especially against Bacillus subtilis ATCC 6633 (MIC = 15.63-250 mu g/mL), Staphylococcus aureus ATCC 25923 (MIC = 31.25-250 mu g/mL), and Micrococcus luteus ATCC 10240 (MIC = 125-250 mu g/mL).

  DOI：

  10.1007/s00044-012-0302-9
• 作为产物：
  描述：

  1-苯甲酰-4-苯基-3-硫代氨基脲 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 11.0h， 生成 ethyl 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetate
  参考文献：
  名称：

  5-芳基-2H-四唑，5-芳基-2H-四唑-2-乙酸和[（4-苯基-5-芳基-4H-1,2,4-三唑-3-基）硫代]的合成乙酸可能是超氧化物清除剂和抗炎药。

  摘要：

  一系列5-芳基-2H-四唑，5-芳基-2H-四唑-2-乙酸和[（4-苯基-5-芳基-4H-1,2,4-三唑-3-基）硫代合成乙酸，并在体外进行角叉菜胶诱导的大鼠爪水肿测定和反向被动Arthus反应中的超氧化物清除活性测试。羟基取代的化合物可以有效地用作超氧化物的体外清除剂，但不能有效地用作体内抗炎剂。

  DOI：

  10.1021/jm00378a007

文献信息

• Alkylation of 1,2,4-triazole-3-thiols with haloalkanoic acid esters
  作者：M. A. Samvelyan、T. V. Ghochikyan、S. V. Grigoryan、R. A. Tamazyan、A. G. Aivazyan

  DOI：10.1134/s1070428017060203

  日期：2017.6

  Alkylation of 4,5-disubstituted 4H-1,2,4-triazole-3-thiols with methyl chloroformate and ethyl chloroacetate chemoselectively afforded the corresponding S-alkyl derivatives, whereas the alkylation of 5-benzyl-4-phenyl-4H-1,2,4-triazole-3-thiol with methyl 3-bromopropanoate gave an inseparable mixture of S- and N-alkylation products. Hydrazinolysis of S-(5-benzyl-4-phenyl-4H-1,2,4-triazol-3-yl) methyl

  4,5-二取代的4 H -1,2,4-三唑-3-硫醇与氯甲酸甲酯和氯乙酸乙酯的烷基化反应产生相应的S-烷基衍生物，而5-苄基-4-苯基-4 H的烷基化-1,2,4-三唑-3-硫醇与3-溴丙酸甲酯形成不可分离的S-和N-烷基化产物混合物。的肼解小号- （5-苄基-4-苯基-4- ħ -1,2,4-三唑-3-基）甲基碳酸酯所涉及的异常裂解与形成的初始4,5-二取代的1,2,4-三唑的和肼甲酸甲酯。
• Synthesis and Characterisation of Some Coumarin-1,2,4-Triazol-3-Thioether Hybrid Molecules
  作者：Fatih Yılmaz、Emre Menteşe

  DOI：10.3184/174751917x14815427219040

  日期：2017.1

  A new series of N′-[(4-methyl/phenyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio]acetyl}-2-oxo-2H-chromene-3-carbohydrazides was synthesised via the reaction of 2-[(4-methyl/phenyl-5-phenyl-4H-1,2,4-triazol-3-yl)thio]acetohydrazides and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones in good yields.

  N′-[(4-甲基/苯基-5-苯基-4H-1,2,4-三唑-3-基)硫代]乙酰}-2-氧代-2H-色烯-3-碳酰肼新系列通过 2-[(4-甲基/苯基-5-苯基-4H-1,2,4-三唑-3-基)硫代]乙酰肼和 3-(1H-苯并三唑-1-基羰基)-反应合成2H-chromen-2-ones 产量良好。
• Synthesis and Antimicrobial Evaluation of New Schiff Base Hydrazones Bearing 1,2,4-Triazole Moiety
  作者：Łukasz Popiołek、Urszula Kosikowska、Monika Wujec、Anna Malm

  DOI：10.1080/10426507.2013.789878

  日期：2014.11.2

  GRAPHICAL ABSTRACT Abstract This study presents the synthesis and spectral analysis of new Schiff base hydrazone derivatives. New compounds were prepared by the reaction of [(4-phenyl-5-substituted-4H-1,2,4-triazol-3-yl)sulfanyl] acetohydrazide with various aldehydes. The structures of the prepared compounds were confirmed by means of 1H NMR, 13C NMR, and elemental analyses. All synthesized compounds

  图形摘要 摘要 本研究介绍了新型席夫碱腙衍生物的合成和光谱分析。通过[(4-苯基-5-取代-4H-1,2,4-三唑-3-基)硫烷基]乙酰肼与各种醛反应制备新化合物。所制备化合物的结构通过1H NMR、13C NMR和元素分析进行​​确认。通过使用琼脂稀释技术针对革兰氏阳性和革兰氏阴性细菌的四种参考菌株和属于念珠菌属的 12 种酵母，筛选所有合成化合物的体外抗菌活性。
• Ismaiel, A. M.; Yousif, M. Y.; Metwally, M. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 5, p. 489 - 491
  作者：Ismaiel, A. M.、Yousif, M. Y.、Metwally, M. A.、El-Kerdawy, M. M.

  DOI：——

  日期：——
• Synthesis, in vitro cytotoxicity, and antibacterial studies of new asymmetric bis-1,2,4-triazoles
  作者：Rohit Singh、Gurubasavaraj V. Pujar、Madhusudan N. Purohit、V. M. Chandrashekar

  DOI：10.1007/s00044-012-0209-5

  日期：2013.5

  A series of asymmetric bis-1,2,4-triazoles (4a-l) were synthesized from respective 1,2,4-triazole-3-thiocarbohydrazides (2a, b) via base catalyzed dehydrative cyclization of thiosemicarbazide intermediates (3a-l). The synthesized compounds were characterized by IR, H-1-NMR, C-13-NMR, and Mass spectral studies. The asymmetric bis-1,2,4-triazole derivatives (4a-l) were evaluated for in vitro antioxidant activity by DPPH radical scavenging assay method. The compounds with significant antioxidant potential were evaluated for in vitro cytotoxicity by MTT assay method against HT29 (Human adenocarcinoma) and MDA-231 (Human breast cancer) cancer cell lines. All the synthesized compounds were evaluated for in vitro antibacterial activity against Bacillus subtilus (ATCC 6633), Staphylococcus aureus (ATCC-25923), Escherichia coli (ATCC-25922), and Pseudomonas aeruginosa (ATCC-27853).