diethyl (3-((5-(4-chlorophenyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate | 1620200-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl (3-((5-(4-chlorophenyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate
• CAS: 1620200-77-2
• 化学式: C₁₅H₂₁ClN₃O₃PS
• 分子量: 389.843
• InChiKey: ODQVPAPFSCJURS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰肼 在 盐酸 、 iron(III) oxide 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 生成 diethyl (3-((5-(4-chlorophenyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate
  参考文献：
  名称：

  Magnetically Recyclable Nano-Fe₂O₃-Catalyzed Chemoselective Synthesis and Antioxidant Activity of Diethyl (3-((5-Aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonates

  摘要：

  An efficient, green, and chemoselective S-alkylation of 5-aryl-1H-1,2,4-triazole-3-thiones with diethyl (3-bromopropyl)phosphonate in water, catalyzed by nano-Fe2O3 under ligand- and base-free conditions, is reported. Clean reaction, less expensive catalyst, excellent yields, and easy workup are the advantages of the present method. The catalyst can be easily collected by a magnet and recycled without significant loss in catalytic activity. The newly synthesized compounds were screened for their antioxidant property by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging assay. The majority of the compounds exhibited good antioxidant activity.

  DOI：

  10.1080/00397911.2014.918146

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。