Chemistry of Heterocycles & Natural Product Research Laboratory, Department of Chemistry, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India.
Chemistry of Heterocycles & Natural Product Research Laboratory, Department of Chemistry, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India.
J Photochem Photobiol B. 2016 Sep;162:232-239. doi: 10.1016/j.jphotobiol.2016.06.051. Epub 2016 Jun 30.
A non-conventional methodology has been utilized for the synthesis of a series of 1,2,4-triazolo-quinazoline-thiones (2a-l). Here the reaction was carried out between 1,2,4-triazolo-quinazolinones (1a-l), in the presence of 1,4-dioxane. The mixture was irradiated under microwave (100W) for 7min to obtain targeted molecules (2a-l). All the synthesized molecules were confirmed by (1)H, (13)C NMR and HRMS. The solvatochromic property (absorption spectra) of compounds (2a-l) in solvents of different polarities was studied. The compounds (2a-l) were further subjected for their in vitro free radical screening using 2,2-diphenyl-1-picrylhydrazyl (DPPH) method and also screened for their in vitro anti-fungal property against Aspergillus flavus (A. flavus) and Aspergillus niger (A. niger). The results from free radical scavenging assay showed promising activity for compounds 2a, e-i, whereas compound 2d showed significant antioxidant activity when compared to ascorbic acid. In vitro anti-fungal study showed that the 1,2,4-triazolo-quinazoline-thiones (2a-l) had significant activity against A. flavus and A. niger compared with widely used antifungal agent Fluconazole.
一种非传统的方法学被用于一系列 1,2,4-三唑并喹唑啉-4-硫酮（2a-l）的合成。在该反应中，1,2,4-三唑并喹唑啉酮（1a-l）在 1,4-二氧六环的存在下进行反应。混合物在微波（100W）下照射 7 分钟以获得目标分子（2a-l）。所有合成的分子都通过 1H、13C NMR 和 HRMS 得到确认。研究了化合物（2a-l）在不同极性溶剂中的溶剂化变色性质（吸收光谱）。进一步将化合物（2a-l）用于 2,2-二苯基-1-苦基肼（DPPH）法的体外自由基筛选，并筛选其对黄曲霉（A. flavus）和黑曲霉（A. niger）的体外抗真菌活性。自由基清除实验的结果表明，化合物 2a、e-i 具有良好的活性，而化合物 2d 的抗氧化活性明显优于抗坏血酸。体外抗真菌研究表明，与广泛使用的抗真菌剂氟康唑相比，1,2,4-三唑并喹唑啉-4-硫酮（2a-l）对黄曲霉和黑曲霉具有显著的活性。
