5-(4-nitrophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione | 93378-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-nitrophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 5-(4-nitro-phenyl)-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione；5-(4-Nitro-phenyl)-4-phenyl-2,4-dihydro-[1,2,4]triazol-3-thion；5-(4-nitrophenyl)-2,4-dihydro-4-phenyl-3H-1,2,4-triazol-3-thione；3-(4-nitrophenyl)-4-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 93378-57-5
• 化学式: C₁₄H₁₀N₄O₂S
• mdl: MFCD00519072
• 分子量: 298.325
• InChiKey: VOABNYQQUDETHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(4-nitrophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 6-bromo-2-(4-nitrophenyl)-3,7-diphenyl-3,5,6,7-tetrahydro[1,2,4]triazolo[5,1-b][1,3]thiazin-8-ium tribromide
  参考文献：
  名称：

  [1,3]噻唑并[3,2-b][1,2,4]三唑-7-鎓和[1,2,4]三唑并[5,1-b][1,3]噻嗪的合成-通过 3-[(2-alken-1-yl) 硫烷基]-4H-1,2,4-三唑的区域选择性亲电环化制备 4-ium 盐

  摘要：

  摘要 [1,3]噻唑并[3,2-b][1,2,4]三唑-7-鎓10和[1,2,4]三唑并[5,1-b]的区域选择性制备方法][1,3]thiazin-4-ium 盐 9 通过 3-[(2-alken-1-yl)sulfanyl]-4H-1,2,4-triazoles 3 的区域选择性亲电环化。亲电杂环化的方向很大程度上取决于烯基取代基的性质。

  DOI：

  10.1515/hc-2015-0158
• 作为产物：
  描述：

  1-(p-nitrobenzoyl)-4-phenyl-3-thiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-(4-nitrophenyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  作为人类 VEGFR-2 和 TB-InhA 双重抑制剂的新型取代 1,2,4-三唑类似物的设计、合成、体外和计算机评估

  摘要：

  [显示省略]

  DOI：

  10.1016/j.bioorg.2023.106883

文献信息

• A One-Pot Synthesis of 4,5-Disubstituted-1,2,4-triazole-3-thiones on Solid Support under Microwave Irradiation
  作者：Shahnaz Rostamizadeh、Kambiz Mollahoseini、Samar Moghadasi

  DOI：10.1080/10426500500542992

  日期：2006.8.1

  from the reaction of acid hydrazide 1 with alkyl or aryl isothiocyanate 2 in the presence of a KOH (10%) solution on the surface of silica gel as well as on the surface of montmorillonite K10 under microwave irradiation. These triazoles have also been prepared from the reaction of 4-substituted-1-aroyl thiosemicarbazides 3a–e, with a KOH (10%) solution on the surface of silica gel under microwave irradiation

  4,5-二-取代-1,2,4-三唑-3-硫酮（4a-f）在一个阶段由酰肼 1 与烷基或芳基异硫氰酸酯 2 在 KOH 存在下反应制备（ 10%) 溶液在硅胶表面和蒙脱石 K10 表面在微波照射下。这些三唑也可以通过 4-取代-1-芳酰基氨基硫脲 3a-e 与硅胶表面上的 KOH (10%) 溶液在微波辐射下反应制备。
• Discovery of Natural Sesquiterpene Lactone 1-<i>O</i>-Acetylbritannilactone Analogues Bearing Oxadiazole, Triazole, or Imidazole Scaffolds for the Development of New Fungicidal Candidates
  作者：Xiao-yan Zhi、Yuan Zhang、Yang-fan Li、Ying Liu、Wen-peng Niu、Yang Li、Cheng-ran Zhang、Hui Cao、Xiao-juan Hao、Chun Yang

  DOI：10.1021/acs.jafc.3c02497

  日期：2023.8.2

  control efficacy of compound 10 against B. cinerea was further studied using infected tomatoes (protective effect = 58.4%; therapeutic effect = 48.7%). The preliminary structure–activity relationship analysis suggested that the introduction of the 1,3,4-oxadiazole moiety (especially the 1,3,4-oxadiazole heterocycle containing the 4-chlorophenyl, 2-furyl, or 2-pyridinyl group) on the skeleton of ABL

  近几十年来，天然产物因其新颖的结构和多种生物活性而被认为是开发新型农用化学品的重要资源。因此，本文使用1- O-乙酰基不列颠尼内酯 (ABL)（一种来自不列颠旋覆花的天然倍半萜内酯）作为进一步修饰的先导物，以发现杀菌候选物。设计并合成了六系列含有恶二唑、三唑或咪唑部分的基于ABL的衍生物，并在体外和体内评估了它们的抗真菌活性。生物测定结果表明，化合物8d、8h和8j（EC 50分别为61.4、30.9和12.4 μg/mL）比其前体ABL（EC 50 > 500 μg/mL）表现出更显着的对尖孢镰刀菌的抑制活性，并且阳性对照海美唑 (EC 50 = 77.2 μg/mL)。衍生物8d和11j（EC 50分别为 19.6 和 41.5 μg/mL）比ABL（EC 50 = 68.3 μg/mL）表现出更有效的抗曼莎胞孢菌活性。化合物10对七种植物病原真菌菌丝体表现出优异的广谱抗真菌活性。特别
• Synthesis, antimicrobial and antioxidant evaluation, and molecular docking study of 4,5-disubstituted 1,2,4-triazole-3-thiones
  作者：Hamid Beyzaei、Maryam Ghanbari Kudeyani、Hojat Samareh Delarami、Reza Aryan

  DOI：10.1016/j.molstruc.2020.128273

  日期：2020.9

  There is a growing need for new antibiotics and antifungal drugs to combat pathogenic bacteria and fungi. In order to develop potential antimicrobial agents, some 1,2,4-triazole-3-thiones were synthesized from the reaction of hydrazides with isothiocyanates under optimized conditions in deep eutectic solvent of potassium carbonate-glycerol (1:5 M ratio). Blocking properties of all products were assessed on a variety of Gram-positive and Gram-negative bacterial as well as fungal pathogens. Good to excellent inhibitory effects especially against fungi were observed with all synthesized compounds. 5-(4-Hydroxyphenyl)-4-(4-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (3b) showed significant antioxidant activity according to the results obtained from 2,2-diphenyl-1-picrylhydrazylf (DPPH) free radical scavenging experiments. The possible interaction mechanism of synthetic triazoles with 1IYL enzyme on Aspergillus fumigatus was investigated by molecular docking method. A complete agreement was found between experimental data and theoretical calculations. Hydrogen bond acceptor strength of N-1 in 1,2,4-triazole rings was the main cause of the observed differences. (C) 2020 Elsevier B.V. All rights reserved.
• Silberg; Cosma, Academia Republicii Populare Romine, Filiala Cluj, Studii si Cercetari de Chimie, 1959, vol. 10, p. 151,160
  作者：Silberg、Cosma

  DOI：——

  日期：——
• XRIPAK, S. M.;KREKA, M. I.;DOBOSH, A. A.;YAKUBETS, V. I., XIMIYA GETEROTSIKL. SOEDIN., 1984, N 6, 843-846
  作者：XRIPAK, S. M.、KREKA, M. I.、DOBOSH, A. A.、YAKUBETS, V. I.

  DOI：——

  日期：——