Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds.
Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds.
复制标题
DOI：
10.3390/molecules22060875
复制
发表时间：
2017-05-25
期刊：
影响因子：
--
通讯作者：
Piotto S
中科院分区：
文献类型：
--
作者：
Concilio S;Sessa L;Petrone AM;Porta A;Diana R;Iannelli P;Piotto S
设计并合成了一些新的(苯基-二氮)苯酚3a-g，用于评价它们的抗菌活性。以先前合成的具有抗细菌和真菌活性的分子为先导，通过引入/移除或置换偶氮苯环上的羟基来修饰和优化结构。这项工作的目的是评估随后发生的抗菌活性变化，并验证对这些化合物来说，合理的机制可能涉及与蛋白质受体的相互作用，而不是与膜的相互作用。所有新合成的化合物均经1H-核磁共振、DSC热分析和UV-Vis光谱确证。测定各化合物对革兰氏阳性菌、革兰氏阴性菌和白色念珠菌的体外最小抑菌浓度(MIC)。化合物3b和3g对金黄色葡萄球菌和白色念珠菌的抑菌活性最高，MIC值分别为10和3µg/mL。构效关系研究能够合理地解释偶氮苯苯环上不同取代基对抗菌活性的影响。
Some novel (phenyl-diazenyl)phenols 3a–g were designed and synthesized to be evaluated for their antimicrobial activity. A previously synthesized molecule, active against bacteria and fungi, was used as lead for modifications and optimization of the structure, by introduction/removal or displacement of hydroxyl groups on the azobenzene rings. The aim of this work was to evaluate the consequent changes of the antimicrobial activity and to validate the hypothesis that, for these compounds, a plausible mechanism could involve an interaction with protein receptors, rather than an interaction with membrane. All newly synthesized compounds were analyzed by 1H-NMR, DSC thermal analysis and UV-Vis spectroscopy. The in vitro minimal inhibitory concentrations (MIC) of each compound was determined against Gram-positive and Gram-negative bacteria and Candida albicans. Compounds 3b and 3g showed the highest activity against S. aureus and C. albicans, with remarkable MIC values of 10 µg/mL and 3 µg/mL, respectively. Structure-activity relationship studies were capable to rationalize the effect of different substitutions on the phenyl ring of the azobenzene on antimicrobial activity.
登录
查看更多内容
影响因子：
5.2
作者：
Piotto, Stefano;Concilio, Simona;Incarnato, Loredana
通讯作者：
Incarnato, Loredana
影响因子：
3.3
作者：
Concilio, Simona;Bugatti, Valeria;Piotto, Stefano Piotto
通讯作者：
Piotto, Stefano Piotto
影响因子：
3.9
作者：
Cariati, F;Caruso, U;Tuzi, A
通讯作者：
Tuzi, A
影响因子：
11.8
作者：
Liu, Catherine;Bayer, Arnold;Chambers, Henry F.
通讯作者：
Chambers, Henry F.
影响因子：
2.2
作者：
Patton, T;Barrett, J;Moran, N
通讯作者：
Moran, N