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Design, synthesis, DNA assessment and molecular docking study of novel 2-(pyridin-2-ylimino)thiazolidin-4-one derivatives as potent antifungal agents.
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2018-11-28 , DOI: 10.1016/j.bioorg.2018.11.050
Nadia Hanafy Metwally 1 , Ibrahim Taha Radwan 2 , Walaa Salah El-Serwy 3 , Mohamed Ahmed Mohamed 4
Affiliation  

A series of novel 2-imino-4-thiazolidinone derivatives 4a,b was synthesized through reaction of unsymmetrical thioureas 3a,b with chloroacetic acid. Condensation of 4a,b with aromatic aldehydes 5a-eyielded the corresponding 5-arylidene derivatives 6a-j. In addition, the reaction of 4a,b with 4-arylazo-3-hydroxybenzaldehydes 8a-c furnished the respective mono-arylazo-4-thiazolidinones10a-f. All the newly synthesized compounds were confirmed by their elemental analysis and spectral data. The antifungal activity of the newly synthesized compounds was assessed and the compounds 6d, 6e, 6i, 6j, 9a,b and 10a-frevealedhigher antifungal activity towards Alternaria solani than to the standard Ridomil gold plus. Moreover, the DNA toxicity of 4-thiazolidinone derivatives 6d, 9a, 10b, 10c and 10f on the nucleic acid of Alternaria solani (KT354939) was performed and the results showed qualitatively more than 70% cleavage. Also, compounds 6i, 6j, 9b, 10c and 10f were docked inside the active site of 1ZOYenzyme and suitable binding with the active site of amino acids, were displayed according to their bond lengths, angles and conformational energy.

中文翻译:

设计,合成,DNA评估和新型2-(吡啶-2-ylimino)噻唑烷酮-4-一衍生物作为有效的抗真菌剂的分子对接研究。

通过不对称硫脲3a,b与氯乙酸反应,合成了一系列新型的2-亚氨基-4-噻唑烷酮衍生物4a,b。4a,b与芳族醛5a缩合,生成相应的5-亚芳基衍生物6a-j。另外,4a,b与4-芳基偶氮-3-羟基苯甲醛8a-c的反应提供了相应的单芳基偶氮-4-噻唑烷酮10a-f。所有新合成的化合物均通过其元素分析和光谱数据证实。评估了新合成的化合物的抗真菌活性,并且化合物6d,6e,6i,6j,9a,b和10a的抗真菌活性比标准Ridomil gold plus高。此外,4-噻唑烷酮衍生物6d,9a,10b,在Solanternate solani(KT354939)的核酸上进行了10c和10f的鉴定,结果定性地显示了超过70%的裂解。同样,化合物6i,6j,9b,10c和10f停靠在1ZOY酶的活性位点内,并根据其键长,角度和构象能显示出与氨基酸活性位点的适当结合。
更新日期:2018-11-28
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