4-(3-chlorophenyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

• 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
• 英文名称: 4-(3-chlorophenyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-(3-chlorophenyl)-3-pyridin-4-yl-1H-1,2,4-triazole-5-thione
• 化学式: C₁₃H₉ClN₄S
• mdl: MFCD01312812
• 分子量: 288.76
• InChiKey: QNMAMRQMXGVQAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 、 4-(3-chlorophenyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.5h， 以57%的产率得到3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-(4-pyridyl)-4-m-chlorophenyl-4H-1,2,4-triazole
  参考文献：
  名称：

  5-(4-吡啶基)-4-芳基-4H-1,2,4-三唑-3-硫醇新S-核苷的合成及分子结构

  摘要：

  描述了 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) 的一些新的 S-核苷的合成。在氢氧化钾存在下，用四-O-乙酰基-aD-吡喃葡萄糖基溴将(4a-n)直接糖基化，然后用甲醇中的无水氨脱乙酰基，得到相应的3-S-(β-D-吡喃葡萄糖基)-5- (4-吡啶基)-4-芳基-4H-1,2,4-三唑(6a-n)，收率良好。通过 1 H NMR、 13 C NMR 光谱和元素分析对所有化合物进行了充分表征。为了帮助解释光谱数据，3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-5-(4-吡啶基)的晶体结构)-4-苯基-4H-1,2,4-三唑(5a)通过X射线衍射测定。

  DOI：

  10.1002/jccs.200800124
• 作为产物：
  描述：

  4-(3-chlorophenyl)-1-(isonicotinoyl)thiosemicarbazide 在 sodium hydroxide 作用下， 生成 4-(3-chlorophenyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  5-(4-吡啶基)-4-芳基-4H-1,2,4-三唑-3-硫醇新S-核苷的合成及分子结构

  摘要：

  描述了 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) 的一些新的 S-核苷的合成。在氢氧化钾存在下，用四-O-乙酰基-aD-吡喃葡萄糖基溴将(4a-n)直接糖基化，然后用甲醇中的无水氨脱乙酰基，得到相应的3-S-(β-D-吡喃葡萄糖基)-5- (4-吡啶基)-4-芳基-4H-1,2,4-三唑(6a-n)，收率良好。通过 1 H NMR、 13 C NMR 光谱和元素分析对所有化合物进行了充分表征。为了帮助解释光谱数据，3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-5-(4-吡啶基)的晶体结构)-4-苯基-4H-1,2,4-三唑(5a)通过X射线衍射测定。

  DOI：

  10.1002/jccs.200800124

文献信息

• Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones
  作者：Mashooq Ahmad Bhat、Mohamed A. Al-Omar、Ahmed M. Naglah、Mohamed M. Abdulla、Hoong-Kun Fun

  DOI：10.1007/s00044-014-1216-5

  日期：2015.4

  The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2a-r) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The single crystal X-ray analysis confirmed the structure of these products as N-4-cyclohexyl/aryl-5-(pyridine-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones (3a-r). The in vitro antitumor activity of compounds was screened against three cell lines; BEL-7402, HUH-7 and HepG2 human hepatoma using MTT assay. Sorafenib (50 A mu M) was used as a positive control. The results of the MTT-dye reduction assay indicated that most of the compounds exert potent cytotoxic/antiproliferative effect in a time and dose-dependent manner via induced apoptosis of HepG2 cells. Results also showed that the tested compounds could significantly enhance the activity of caspase-3 which plays a very important role as the central effecter during apoptosis. The effect of different substitutions on the aromatic portion on the activity was found to be in the following order CH3 > OCH3 > I > SO2NH2 > OC2H5 > C2H5 > NO2 > Cl > CH3CONH.
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODE-GENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Sheridan Joseph M.

  公开号：US20140031547A1

  公开（公告）日：2014-01-30

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Electrophoretics Limited

  公开号：US20160354375A1

  公开（公告）日：2016-12-08

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• Synthesis and Molecular Structure of New S-Nucleosides of 5-(4-Pyridyl)-4-Aryl-4<i>H</i>-1,2,4-Triazole-3-Thiols
  作者：Huan-Huan Zhang、Xiu-Qin Hu、Gui-Fang Fan、Peng-Fei Xu

  DOI：10.1002/jccs.200800124

  日期：2008.8

  The synthesis of some new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) is described. Direct glycosylation of (4a-n) with tetra-O-acetyl-a-D-glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3-S-(β-D-glucopyranosyl)-5-(4-pyridyl)-4-aryl-4H-1,2,4-triazoles (6a-n) in good yields. All the

  描述了 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) 的一些新的 S-核苷的合成。在氢氧化钾存在下，用四-O-乙酰基-aD-吡喃葡萄糖基溴将(4a-n)直接糖基化，然后用甲醇中的无水氨脱乙酰基，得到相应的3-S-(β-D-吡喃葡萄糖基)-5- (4-吡啶基)-4-芳基-4H-1,2,4-三唑(6a-n)，收率良好。通过 1 H NMR、 13 C NMR 光谱和元素分析对所有化合物进行了充分表征。为了帮助解释光谱数据，3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-5-(4-吡啶基)的晶体结构)-4-苯基-4H-1,2,4-三唑(5a)通过X射线衍射测定。
• Pyridine-Based 1,2,4-Triazolo-Tethered Indole Conjugates Potentially Affecting TNKS and PI3K in Colorectal Cancer
  作者：Prasanna A. Yakkala、Samir R. Panda、Vegi G. M. Naidu、Syed Shafi、Ahmed Kamal

  DOI：10.1021/acsmedchemlett.2c00475

  日期：2023.3.9