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Antimicrobial Potential of Chiral Amide Derivatives of Ricinoleic and 3‐Hydroxynonanoic Acid
The Journal of the American Oil Chemists’ Society ( IF 2 ) Pub Date : 2019-10-04 , DOI: 10.1002/aocs.12292
Sylwia Matysiak 1 , Julia Zabielska 2 , Józef Kula 1 , Alina Kunicka‐Styczyńska 2
Affiliation  

The growing role of fatty acid amides in medicinal chemistry has recently been observed. Therefore, using simple and fast methods, a series of chiral amide derivatives (24 compounds) of ricinoleic and 3‐hydroxynonanoic acid was obtained with 31–95% yields. Then, the evaluation of their antimicrobial activity against 13 microorganisms representing Gram‐positive and Gram‐negative bacteria, yeast, and molds was performed. The obtained compounds showed antimold potential; however, the tested species of molds were more susceptible to derivatives of 3‐hydroxynonanoic acid than to amides obtained from ricinoleic acid (RA). Interestingly, hydroxamic acids derived from RA exhibited the best activity against Candida albicans and Candida tropicalis. On the other hand, hydroxamic acids derived from 3‐hydroxynonanoic acid showed the best antimicrobial potential against the remaining tested microorganisms, especially against Pseudomonas cedrina. The obtained derivatives can be considered compounds of potential pharmacological significance, which is important due to the increasing problem of microbial resistance.

中文翻译:

蓖麻油酸和3-羟基壬酸的手性酰胺衍生物的抗菌潜力

最近已经观察到脂肪酸酰胺在药物化学中的作用越来越大。因此,使用简单快速的方法,可以得到一系列蓖麻油酸和3-羟基壬酸的手性酰胺衍生物(24种化合物),产率为31–95%。然后,评估了它们对代表革兰氏阳性和革兰氏阴性细菌,酵母菌和霉菌的13种微生物的抗菌活性。所获得的化合物显示出抗霉变的潜力。但是,测试过的霉菌种类对3-羟基壬酸衍生物的敏感性要高于从蓖麻油酸(RA)获得的酰胺。有趣的是,源自RA的异羟肟酸对白色念珠菌热带念珠菌表现出最好的活性。。另一方面,衍生自3-羟基壬酸的异羟肟酸对其余测试微生物,尤其是对雪松假单胞菌具有最佳的抗菌潜力。所获得的衍生物可以被认为是具有潜在药理学意义的化合物,由于日益增加的微生物抗性问题,这是重要的。
更新日期:2020-01-06
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