5-(3,4-dimethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-thione | 146198-05-2

• 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-(3,4-dimethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-thione
• 英文别名: 5-(3,4-dimethoxyphenyl)-1,2-dihydro-1,2,4-triazole-3-thione
• CAS: 146198-05-2
• 化学式: C₁₀H₁₁N₃O₂S
• mdl: MFCD00617774
• 分子量: 237.282
• InChiKey: GOAFWCLLGUXBRK-UHFFFAOYSA-N

物化性质

• 沸点：
  341.2±52.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)
• 溶解度：
  18.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-thione 在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 Acetic acid 2-(3,4-dimethoxy-phenyl)-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]thiazin-6-yl ester
  参考文献：
  名称：

  Foks; Rudnicka; Glowka, Pharmazie, 1992, vol. 47, # 10, p. 770 - 773

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酸甲酯 在 盐酸 、 一水合肼 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 5-(3,4-dimethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-thione
  参考文献：
  名称：

  Synthesis of New S-alkylated-3-mercapto-1,2,4-triazole Derivatives Bearing Cyclic Amine Moiety as Potent Anticancer Agents

  摘要：

  一系列3-[3-[4-(取代)-1-环胺]丙基]硫-5-取代[1,2,4]三唑(8a-j)，从相应的羧酸出发，以良好的收率被合成。这些衍生物对五种不同的人类癌细胞系进行了细胞毒性研究。三种化合物显示出良好的抗癌活性。三唑衍生物，8i和8j，对U937和HL-60细胞尤其有效。化合物的细胞毒性效力在不同细胞系之间有所变化，这表明这些化合物的结构特性可能是其生物活性的可能决定因素。

  DOI：

  10.2174/157018012799129882

文献信息

• An Efficient Nonconventional Glycerol-Based Solid Acid Catalyzed Synthesis and Biological Evaluation of Phosphonate Conjugates of 1,2,4-triazole Thiones
  作者：Madugula S. R. Murty、Mohana R. Katiki、Busam R. Rao、Sai S. Narayanan、Ruby J. Anto、Sudhreer K. Buddana、Reddy S. Prakasham、Bethala L. A. P. Devi、Rachapudi B. N. Prasad

  DOI：10.2174/1570180813666160125222334

  日期：2016.10.3

  A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a–t) has been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H-1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon catalyst derived from glycerol. In addition, a facile and green approach for the esterification of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines (HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial activities of the synthesized compounds were investigated against four bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains: Aspergillus niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal activity with high inhibition zone diameter compared to the standard drug.

  一系列二乙基（3-（（5-芳基-1H-1,2,4-三唑-3-基）硫代）丙基）膦酸酯（7a–t）通过使用由甘油衍生的高效、绿色且非传统的SO3H碳固体催化剂，将二乙基（3-溴丙基）膦酸酯与5-芳基-1H-1,2,4-三唑-3-硫酮耦合合成，产率极佳。此外，还报道了一种利用甘油基固体酸催化剂进行羧酸酯化的简便且绿色的方法。合成的化合物的结构通过IR、NMR和HRMS研究进行了表征。这些三唑衍生物通过标准的MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴）法对五种不同的人类癌细胞系（HeLa：宫颈，A549：肺，A375：皮肤，MDA-MB-231：乳腺和T98G：脑）进行了体外细胞毒性筛选。合成的化合物的抗菌活性对四种细菌菌株：枯草杆菌、金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌和三种真菌菌株：黑曲霉、土曲霉、烟曲霉进行了研究。初步结果表明，化合物7f显示出最大的抗癌活性，而化合物7d、7e、7f、7m和7q表现出中等抗菌活性。化合物7g、7h、7o和7p显示出良好的抗真菌活性，抑制区直径相比标准药物较大。
• New Sulfanilamide Derivatives Incorporating Heterocyclic Carboxamide Moieties as Carbonic Anhydrase Inhibitors
  作者：Andrea Angeli、Victor Kartsev、Anthi Petrou、Mariana Pinteala、Roman M. Vydzhak、Svitlana Y. Panchishin、Volodymyr Brovarets、Viviana De Luca、Clemente Capasso、Athina Geronikaki、Claudiu T. Supuran

  DOI：10.3390/ph14080828

  日期：——

  of activity. We report here a novel series of sulfanilamide derivatives containing heterocyclic carboxamide moieties which were evaluated as CA inhibitors against the physiological relevant isoforms hCA I, II, IX, and XII. Some of them showed selectivity toward isoform hCA II and hCA XII. Molecular docking was performed for some of these compounds on isoforms hCA II and XII to understand the possible

  碳酸酐酶 (CA) 是普遍存在的金属酶，涉及多种疾病。有 15 种人类 CA (hCA) 亚型，它们的高度同源性对发现没有脱靶副作用的潜在药物提出了挑战。出于这个原因，正在进行许多合成和药理学研究工作，以实现 CA 活性调节剂的全部药理学潜力。我们在这里报告了一系列含有杂环甲酰胺部分的新型磺胺衍生物，这些衍生物被评估为针对生理相关亚型 hCA I、II、IX 和 XII 的 CA 抑制剂。其中一些对同种型 hCA II 和 hCA XII 显示出选择性。对这些化合物中的一些在同种型 hCA II 和 XII 上进行了分子对接，以了解与活性位点氨基酸残基的可能相互作用，
• Synthesis, characterization, and anticancer studies of S and N alkyl piperazine-substituted positional isomers of 1,2,4-triazole derivatives
  作者：M. S. R. Murty、Kesur R. Ram、B. Ramalingeswara Rao、Rayudu Venkateswara Rao、Mohana Rao Katiki、Janapala Venkateswara Rao、R. Pamanji、L. R. Velatooru

  DOI：10.1007/s00044-013-0757-3

  日期：2014.4

  A series of 3-[3-[4-(substituted)-1-cyclicamine]propyl]thio-5-substituted[1,2,4]triazoles (8a-m) and 2-[3-[4-(substituted)-1-cyclicamine]propyl]-5-(substituted)-2,4-dihydro-3H[1,2,4]triazole-3-thiones (9a-h) were synthesized with good yields starting from corresponding carboxylic acids using two different methods. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Six compounds had shown good anticancer activity. The triazole derivatives, 9d, 8j, and 8i were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinant of their biological activity.
• Labanauskas; Kalcas; Udrenaite, Pharmazie, 2001, vol. 56, # 8, p. 617 - 619
  作者：Labanauskas、Kalcas、Udrenaite、Gaidelis、Brukstus、Dauksas

  DOI：——

  日期：——
• US5489598A
  申请人：——

  公开号：US5489598A

  公开（公告）日：1996-02-06