Synthesis and antimicrobial activity of some benzoxazinoids derivatives of 2-nitrophenol and 3-hydroxy-2-nitropyridine.

Autor: Lima, William Gustavo, dos Santos, Flávio José, Cristina Soares, Adriana, Macías, Francisco A., Molinillo, José M. G., Maria Siqueira Ferreira, Jaqueline, Máximo de Siqueira, João
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Zdroj: Synthetic Communications; 2019, Vol. 49 Issue 2, p286-296, 11p, 4 Diagrams, 3 Charts
Abstrakt: Benzoxazinoids (BXs), alkaloids frequently found in Gramineae species, are natural defensives that can potentially be exploited to the development of novel antimicrobial agents. Here, BXs analogs were synthesized from 2-nitrophenol (benzoxazinone series) and 3-hydroxy-2-nitropyridine (pyridoxazinone series) and tested against fungal and bacteria of medical interest. The starting materials were submitted to adequate nucleophilic substitution in order to functionalize of analogs, followed by a reductive cyclization catalyzed by palladium on carbon. Next, the biological assays showed that pyridoxazinone serie has a good antibacterial activity, especially against Enterococcus faecalis (Minimum inhibitory concentration—MIC: 7.8-15.6 μg.mL−1) and Acinetobacter baumannii (MIC 31.25-125 μg.mL−1). Antifungal activity, in turn, was related to compound 2e which showed a MIC of 62.5 μg.mL−1 against Candida albicans, Candida glabrata, and Candida tropicalis. All analogs complied with Lipinski's rules and were predicted to have a low toxicity. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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