RK University, Rajkot, India.
Folia Med (Plovdiv). 2021 Feb 28;63(1):105-112. doi: 10.3897/folmed.63.e52655.
Nowadays, researchers are progressively concentrated to generate economical, affordable and also greener synthesis approach for the synthesis of various heterocycles. On look at the beauty of coumarin molecules and oxazoles, it seems to be lead molecules in the anti-microbial area.
With the target to identify efficient molecules, we studied 2-oxo-2H-chromen-4-yl-2-((5-substituted aryl-1,3,4-oxadiazol-2-yl) thio)acetate derivatives using two synthetic protocol/methods, i.e. conventional synthesis and microwave-based synthesis.
Two simultaneous methods, i.e. conventional and microwave synthesis have been used for the synthe-sis of 2-oxo-2H-chromen-4-yl-2-((5-substituted aryl-1,3,4-oxadiazol-2-yl)thio)acetate (6a-l) derivatives. The desired molecules were synthesized by conventional and microwave synthesis and a comparative study was carried out to identify an easy route for industrial applications. The confirmations of the compounds were carried out by spectroscopic techniques such as IR, 1H NMR, 13C NMR, mass spectra and elemental analysis.
All synthesized compounds were evaluated for their in-vitro antibacterial activity against gram-positive bacteria (Staphylococcus aureus, Staphylococcus pyogenes), gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), and antifungal activity (Candida albicans, Aspergillus niger).
All conventional synthesis of final coumarin derivatives were completed within 4-6 h. While that of microwave-based reaction took comparatively more reaction time. Surprisingly, the compounds 6f and 6g could not be synthesized by microwave radiation even after 32 minutes of irradiation. As to the medicinal application part, microbial evaluation of synthesized analogues showed that the compounds 6b, 6e, 6d, and 6j were found more potent in comparison to the reference drug.
如今,研究人员越来越专注于开发经济、实惠且更环保的合成方法,以合成各种杂环化合物。鉴于香豆素分子和恶唑的优点,它们似乎是抗菌领域的主导分子。
为了寻找有效的分子,我们研究了 2-氧代-2H-色烯-4-基-2-((5-取代芳基-1,3,4-恶二唑-2-基)硫代)乙酸酯衍生物,使用了两种合成方案/方法,即常规合成和基于微波的合成。
使用两种同时的方法,即常规和微波合成,合成了 2-氧代-2H-色烯-4-基-2-((5-取代芳基-1,3,4-恶二唑-2-基)硫代)乙酸酯(6a-l)衍生物。通过常规和微波合成合成了所需的分子,并进行了比较研究,以确定一种适用于工业应用的简单途径。通过光谱技术(如 IR、1H NMR、13C NMR、质谱和元素分析)对化合物进行了确认。
所有合成的化合物都进行了体外抗菌活性测试,针对革兰氏阳性菌(金黄色葡萄球菌、化脓性链球菌)、革兰氏阴性菌(大肠杆菌、铜绿假单胞菌)和抗真菌活性(白色念珠菌、黑曲霉)进行了评估。
所有常规合成的最终香豆素衍生物都在 4-6 小时内完成。而基于微波的反应则需要更长的反应时间。令人惊讶的是,即使经过 32 分钟的辐射,化合物 6f 和 6g 也不能通过微波辐射合成。就药用应用部分而言,合成类似物的微生物评估表明,与参考药物相比,化合物 6b、6e、6d 和 6j 更为有效。