One‐pot synthesis of new hydantoin (thiohydantoin) derivatives and evaluation of their antibacterial and antioxidant activities,Journal of Heterocyclic Chemistry

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One‐pot synthesis of new hydantoin (thiohydantoin) derivatives and evaluation of their antibacterial and antioxidant activities
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-08-05 , DOI: 10.1002/jhet.4120
Leila Ghasempour ₁ , Sakineh Asghari _{1,

2} , Mahmood Tajbakhsh ₁ , Mojtaba Mohseni _{2,

3}

Affiliation

One‐pot four‐component reactions of phenacyl bromides, parabanic or thioparabanic acids, thiophenols, and triphenylphosphine in the presence of triethylamine afforded new derivatives of hydantoin or thiohydantoin in good to high yields (65%‐90%). Their antibacterial activities were evaluated against two Gram‐positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa). Among the synthesized compounds, the obtained products from 2‐hydroxythiophenol exhibited higher antibacterial activity than those obtained from 2‐aminothiophenol. Compound 9l including N,N′^′‐diphenyl thiohydantoin moiety showed the highest antibacterial activity (26.0 ± 01.4) against B subtilis, in comparison with other synthesized samples. The antioxidant activities of the synthesized hydantoins and thiohydantoins were investigated by DPPH radical‐scavenging based on Blois method. The results showed that all the compounds have high DPPH inhibition potency (77.4%‐83.9%) that it could be due to existence of heteroatoms with lone pair electrons and exchangeable protons on their NH₂ and OH groups.

中文翻译：

新的乙内酰脲（thiohydantoin）衍生物的一锅法合成及其抗菌和抗氧化活性的评估

在三乙胺的存在下，苯甲酰溴，对羟基苯甲酸酯或对羟基苯甲酸酯的四锅反应，苯酚或三苯膦以高到高的产率提供了乙内酰脲或乙内酰脲的新衍生物（65％-90％）。对两种革兰氏阳性细菌（金黄色葡萄球菌和枯草芽孢杆菌）和两种革兰氏阴性细菌（大肠杆菌和铜绿假单胞菌）的抗菌活性进行了评估。在合成的化合物中，由2-羟基苯硫酚制得的产品比从2-氨基硫酚制得的产品具有更高的抗菌活性。包括N，N' ^'的化合物9l与其他合成样品相比，二苯基硫代乙内酰脲部分对枯草芽孢杆菌显示最高的抗菌活性（26.0±01.4）。通过基于布卢瓦（Blois）法的DPPH自由基清除作用，研究了合成的乙内酰脲和乙内酰脲的抗氧化活性。结果表明，所有化合物均具有较高的DPPH抑制潜能（77.4％-83.9％），这可能是由于在NH ₂和OH基团上存在具有孤对电子和可交换质子的杂原子所致。

更新日期：2020-08-05

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