3H-1,2,4-三唑-3-硫酮,4-[[(4-氯苯基)亚甲基]氨基]-2,4-二氢-5-(4-吡啶基)- | 133847-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3H-1,2,4-三唑-3-硫酮,4-[[(4-氯苯基)亚甲基]氨基]-2,4-二氢-5-(4-吡啶基)-
• 英文名称: 4[{1-(4'-chlorophenyl)methylidine}amino]-3-(4-pyridyl)-5-mercapto-4-1,2,4-triazole
• 英文别名: 4-(4-chlorobenzylideneamino)-3-mercapto-5-pyridin-4-yl-4H-1,2,4-triazole；4-(4-chlorobenzylideneamino)-5-(pyridine-4-yl)-4H-1,2,4-triazole-3-thiol；4-[(4-chlorophenyl)methylideneamino]-3-pyridin-4-yl-1H-1,2,4-triazole-5-thione
• CAS: 133847-01-5
• 化学式: C₁₄H₁₀ClN₅S
• 分子量: 315.786
• InChiKey: NNTKJHMNFPJZBF-UHFFFAOYSA-N

物化性质

• 熔点：
  322 °C(Solv: acetic acid (64-19-7))
• 沸点：
  452.0±51.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3H-1,2,4-三唑-3-硫酮,4-[[(4-氯苯基)亚甲基]氨基]-2,4-二氢-5-(4-吡啶基)- 、 氯乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.17h， 以70%的产率得到ethyl 6-(4-chlorophenyl)-3-pyridin-4-yl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylate
  参考文献：
  名称：

  合成新型 1,2,4-三唑并 [3,4-b][1,3,4] 噻二嗪的高效便捷方案

  摘要：

  新型三唑噻二嗪类似物 5a-p 是通过多步合成序列获得的，从 5-取代的 4-氨基-1,2,4-三唑-3-硫醇 1 开始。化合物 1，在乙酸中与各种芳香醛 2 反应，提供希夫碱 3a–p。在室温下，在氢化钠存在下，3a-p 与氯乙酸乙酯 4 环化得到三唑噻二嗪 5a-p，收率良好。

  DOI：

  10.1080/00397910903261387
• 作为产物：
  描述：

  potassium 4-pyridinyldithiocarbazate 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.09h， 生成 3H-1,2,4-三唑-3-硫酮,4-[[(4-氯苯基)亚甲基]氨基]-2,4-二氢-5-(4-吡啶基)-
  参考文献：
  名称：

  Majumder, Sujan; Bashyal, Bishnu Maya; Gupta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274

  摘要：

  DOI：

文献信息

• Synthesis, anti-inflammatory, analgesic, and antibacterial activities of some triazole, triazolothiadiazole, and triazolothiadiazine derivatives
  作者：Mostafa A. Hussein、Refaat M. Shaker、Mohammed A. Ameen、Mohammed F. Mohammed

  DOI：10.1007/s12272-011-0802-z

  日期：2011.8

  of 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole 1 with the appropriate aldehyde. Compounds 4a–i were synthesized in a one pot reaction involving compounds 3a–i, formaldehyde, and morpholine. Condensation of compound 1 with the appropriate acids or 4-substituted phenacyl bromide gave compounds 6a–d and 8a–f respectively. The chemical structures of the newly synthesized derivatives were elucidated

  本研究涉及新的 1,2,4-三唑、1,3,4-噻二唑和 1,3,4-噻二嗪衍生物的合成。衍生物 3a–i 是通过 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole 1 与适当的醛缩合获得的。化合物 4a-i 是在涉及化合物 3a-i、甲醛和吗啉的一锅反应中合成的。化合物 1 与适当的酸或 4-取代苯甲酰溴缩合分别得到化合物 6a-d 和 8a-f。使用不同的光谱和元素分析方法阐明了新合成衍生物的化学结构。评估了所有化合物的抗炎活性，并使用吲哚美辛作为参考药物测试了最有效的衍生物的镇痛活性。此外，评估了大多数活性化合物的致溃疡性和 LD50。此外，研究了新合成衍生物的抗菌活性。
• SYNTHESIS AND In vitro ANTIMICROBIAL ACTIVITY OF SOME TRIAZOLE DERIVATIVES
  作者：RAVINESH MISHRA、RAJIV KUMAR、SURESH KUMAR、JASEELA MAJEED、MOHD RASHID、SAMEER SHARMA

  DOI：10.4067/s0717-97072010000300019

  日期：——

  Some 4-[1-(substituted)methylidine}-amino]-3-(4-pyridyl)-5-mercapto-4H-1,2,4-triazol (3a- 3f) and N-[5-(4-substituted)-1H-1,2,3-triazol-1-yl]isonicotinamide derivatives (5a- 5e) were synthesized by a sequence of reactions starting from isonicotinic acid hydrazide and is illustrated in scheme 1 and 2. The antibacterial and anti fungal activities of newly synthesized compounds were tested by the disc diffusion method using nutrient agar medium against various microorganisms such as gram positive Staphylococcus aureus and Bacillus subtilis, gram negative Escherichia coli and the fungi Aspergillus niger and Candida albicans. Ciprofloxacin and Fluconazole at 50 mu g/mL were used as standard drugs for antibacterial and antifungal activities, respectively. All the synthesized compounds showed significant activity against various microorganisms.
• Sabale, Prafulla M.; Mehta, Pooja, Indian Journal of Heterocyclic Chemistry, 2013, vol. 23, # 2, p. 149 - 154
  作者：Sabale, Prafulla M.、Mehta, Pooja

  DOI：——

  日期：——
• Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5-mercapto-1,2,4-triazole moiety
  作者：Hamid Khanmohammadi、Mohammad H. Abnosi、Ali Hosseinzadeh、Malihe Erfantalab

  DOI：10.1016/j.saa.2008.05.003

  日期：2008.12

  A series of new Schiff base hydrazones (compounds 1-16) were synthesized by condensation reaction of 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole with various aldehydes and/or dialdehydes. The structure of the prepared compounds was confirmed by means of H-1 NMR, C-13 NMR, UV-vis, IR and elemental analyses. The all prepared compounds were assayed for antibacterial (Escherichia coli and Staphylococcus aureus) and antifungal (Candida albicans) activities by disc diffusion method. The results indicate that all tested compounds did not show any antibacterial activity against E. coli, as gram negative bacteria, and antifungal activity against C albicans. But the compounds 2, 3, 4. 6 and 8 containing 4-Cl. 4-Me, 4-MeO, 2,4-di-Cl and 2-OH substituted phenyl moiety, respectively, showed good inhibition against S. aureus as compare to standard drugs. The structure of all biologically active compounds has also been theoretically studied by ab initio Hartree-Fock (HF) methods. (c) 2008 Elsevier B.V. All rights reserved.
• Majumder, Sujan; Bashyal, Bishnu Maya; Gupta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 10, p. 1260 - 1274
  作者：Majumder, Sujan、Bashyal, Bishnu Maya、Gupta

  DOI：——

  日期：——