Department of Chemistry, R.T.M. Nagpur University, Nagpur 440033, India.
Islamic University of Science and Technology, Kashmir 192122, India.
J Adv Res. 2015 Nov;6(6):941-8. doi: 10.1016/j.jare.2014.10.007. Epub 2014 Nov 1.
An efficiently simple protocol for the synthesis of methyl 7 amino-4-oxo-5-phenyl-2-thioxo-2, 3, 4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates via one-pot three component condensation pathway is established via microwave irradiation using varied benzaldehyde derivatives, methylcyanoacetate and thio-barbituric acid in water as a green solvent. A variety of functionalized substrates were found to react under this methodology due to its easy operability and offers several advantages like, high yields (78-94%), short reaction time (3-6 min), safety and environment friendly without used any catalyst. The synthesized compounds (4a-4k) showed comparatively good in vitro antimicrobial and antifungal activities against different strains. The Compounds 4a, 4b, 4c, 4d 4e and 4f showed maximum antimicrobial activity against Staphylococcus aureus, Bacillus cereus (gram-positive bacteria), Escherichia coli, Klebshiella pneumonia, Pseudomonas aeruginosa (gram-negative bacteria). The synthesized compound 4f showed maximum antifungal activity against Aspergillus Niger and Penicillium chrysogenum strains. Streptomycin is used as standard for bacterial studies and Mycostatin as standards for fungal studies. Structure of all newly synthesized products was characterized on the basis of IR, (1)H NMR, (13)C NMR and mass spectral analysis.
建立了一种通过微波辐射,利用不同的苯甲醛衍生物、甲基氰乙酸酯和硫代巴比妥酸在水中作为绿色溶剂一锅法三组分缩合途径高效简单合成 7-氨基-4-氧代-5-苯基-2-硫代-2,3,4,5-四氢-1H-吡喃并[2,3-d]嘧啶-6-羧酸甲酯的方法。由于其易于操作,该方法可以使各种功能化底物发生反应,并具有许多优点,例如产率高(78-94%)、反应时间短(3-6 分钟)、安全环保,无需使用任何催化剂。合成的化合物(4a-4k)表现出较好的体外抗微生物和抗真菌活性,对不同的菌株都有抑制作用。化合物 4a、4b、4c、4d、4e 和 4f 对金黄色葡萄球菌、蜡状芽孢杆菌(革兰氏阳性菌)、大肠杆菌、肺炎克雷伯菌、铜绿假单胞菌(革兰氏阴性菌)具有最大的抗菌活性。合成的化合物 4f 对黑曲霉和产黄青霉菌株显示出最大的抗真菌活性。链霉素用于细菌研究的标准,制霉菌素用于真菌研究的标准。所有新合成产物的结构均基于 IR、(1)H NMR、(13)C NMR 和质谱分析进行了表征。