(4,5-二苯基-4H-[1,2,4]噻唑-3-磺酰基)-乙酸肼 | 49656-91-9

• 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-磺酰基)-乙酸肼
• 英文名称: [(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetohydrazide
• 英文别名: 2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetohydrazide；2-[(4,5-diphenyl-1,2,4-triazol-3-yl)sulfanyl]acetohydrazide
• CAS: 49656-91-9
• 化学式: C₁₆H₁₅N₅OS
• mdl: MFCD00518988
• 分子量: 325.394
• InChiKey: WDPSOMKCCCJRCE-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C(Solv: ethanol (64-17-5))
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  31 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (4,5-二苯基-4H-[1,2,4]噻唑-3-磺酰基)-乙酸肼 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 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：

  硫代异氰酸苯酯 在 potassium carbonate 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (4,5-二苯基-4H-[1,2,4]噻唑-3-磺酰基)-乙酸肼
  参考文献：
  名称：

  一些香豆素-1,2,4-三唑-3-硫醚杂化分子的合成与表征

  摘要：

  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。

  DOI：

  10.3184/174751917x14815427219040

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 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。
• Synthesis, Dissociation Constants, and Some Pharmacological Properties of Schiff Base Hydrazones and their Cyclization to 1,3-Thiazolidin-4-one Derivatives
  作者：Ł. Popiołek、A. Chodkowska、A. Tryka、K. Pawłowski、M. Kiełczykowska、J. Kocot、M. Wujec、E. Jagiełło-Wójtowicz

  DOI：10.1002/jhet.2257

  日期：2015.9

  This study presents the synthesis, dissociation constants, and pharmacological properties of Schiff base hydrazones. The derivatives were synthesized by the condensation reaction of carboxylic acid hydrazides containing 1,2,4‐triazole system with various aldehydes. The new derivatives of 1,3‐thiazolidin‐4‐one were prepared by the cyclization reaction of Schiff base hydrazones with the mercaptoacetic

  这项研究提出了席夫碱的合成，离解常数和药理特性。通过将含有1,2,4-三唑系统的羧酸酰肼与各种醛进行缩合反应合成衍生物。在1,4-二恶烷存在下，席夫碱与巯基乙酸的环化反应制备了1,3-噻唑烷丁-4-酮的新衍生物。借助于1 H NMR和13 C NMR光谱确认所有获得的化合物的结构。使用分光光度法测定解离常数。四个合成希夫碱腙效果6，7，11和12 在行为测试中对小鼠的中枢神经系统进行了检查。
• 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).