Synthesis and Pharmacological Activities of Oxadiazole and Pyrimidine Bearing Thiocoumarin Derivatives

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY
Monika R. Tiwari, N. Patel
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引用次数: 1

Abstract

The study aims to synthesize thiocoumarin scaffolds clubbed with pyrimidine and 1,3,4-oxadiazole ring system under microwave irradiation and describe their pharmacological activities. We report herein an efficient and simple Lewis acid-catalyzed procedure for the synthesis of novel series of thiocoumarin clubbed with pyrimidine and 1,3,4-oxadiazole motifs under microwave irradiation. The microwave-assisted technique has many advantages, such as a higher yield, a clean and selective procedure, shorter reaction time, and simple work-up. The objective of the present study is to design and synthesize thiocoumarin scaffolds clubbed with pyrimidine and 1,3,4-oxadiazole ring system by microwave-assisted heating. Our prime focus is to highlight the synthetic approach developed for the synthesis of heterocyclic moieties of pharmacological interest, and the prominence has also been given to distinct advantages provided by microwave heating. Thiocoumarin clubbed with pyrimidine, and 1,3,4-oxadiazole motifs was synthesized under microwave irradiation. All the synthesized molecules were evicted by IR, 1H NMR, 13C NMR, and mass spectra. The anti-microbial activity of synthesized compounds was examined against two Gram-negative bacteria (E. coli, P. aeruginosa), two Gram-positive bacteria (S. aureus, S. pyogenes), and three fungi (C. albicans, A. niger, A. clavatus) using the MIC (Minimal Inhibitory Concentration) method, anti-tubercular activity H37Rv using L. J. Slope Method and anti- oxidant activity using DPPH and ABTS bioassay method. The application of microwave technology for the rapid synthesis of biologically significant thiocoumarin analogues is very promising because of its shorter reaction time and higher yield. Some of these new derivatives showed moderate to good in-vitro anti-bacterial, anti-fungal, and anti-tubercular activity. Compounds B4 and B7 appeared to have high radical scavenging efficacies as 35.32 ± 0.446 and 33.97 ± 1.069 μg/mL ± SD of IC50 values in DPPH and ABTS bioassay, respectively. Microwave-assisted synthesis provides an implicit way to discover a promising class of molecular entities for the development of new anti-microbial and anti-oxidant agents. Oxadiazole and pyrimidine bearing thiocoumarin derivatives showed improved anti-microbial, antitubercular, and anti-oxidant activity.
含恶二唑和嘧啶硫代香豆素衍生物的合成及其药理活性
本研究目的是在微波照射下合成嘧啶- 1,3,4-恶二唑环系硫代香豆素支架,并描述其药理活性。本文报道了一种在微波辐射下高效、简单的Lewis酸催化合成嘧啶和1,3,4-恶二唑基序的新型硫代香豆素系列化合物。微波辅助技术具有收率高、工艺干净、选择性好、反应时间短、后处理简单等优点。本研究的目的是设计和合成巯基香豆素-嘧啶- 1,3,4-恶二唑环体系的微波辅助加热支架。我们的主要重点是强调为合成具有药理意义的杂环基团而开发的合成方法,并且也突出了微波加热提供的独特优势。在微波辐射下合成了巯基香豆素与嘧啶和1,3,4-恶二唑基序。所有合成的分子通过IR、1H NMR、13CNMR和质谱进行了分离。测定了合成的化合物对2种革兰氏阴性菌(大肠杆菌、铜绿假单胞菌)、2种革兰氏阳性菌(金黄色葡萄球菌、金黄色葡萄球菌)的抑菌活性。MIC (minimum inhibityconcentration)法测定3种真菌(C. albicans, A. niger, A. clavatus), L. J. Slope法测定抗结核活性H37Rv, DPPH和ABTS生物测定法测定抗氧化活性。微波技术具有反应时间短、产率高的优点,在快速合成具有重要生物学意义的硫代香豆素类似物方面具有广阔的应用前景。这些新的衍生物显示出中等到良好的体外抗菌、抗真菌和抗结核活性。化合物B4和B7具有较强的自由基清除能力,DPPH和ABTS的IC50值分别为35.32±0.446和33.97±1.069 μg/mL±SD。微波辅助合成为开发新的抗微生物和抗氧化剂提供了一种潜在的方法来发现一类有前途的分子实体。含恶二唑和嘧啶的硫代香豆素衍生物具有较好的抗微生物、抗结核和抗氧化活性。
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来源期刊
Current Microwave Chemistry
Current Microwave Chemistry CHEMISTRY, MULTIDISCIPLINARY-
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