Synthesis of nitrogen-containing monoterpenoids with antibacterial activity
Synthesis of nitrogen-containing monoterpenoids with antibacterial activity
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DOI：
10.1080/14786419.2018.1548456
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发表时间：
2020-04-17
影响因子：
2.2
通讯作者：
Lochynski, Stanislaw
中科院分区：
文献类型：
--
作者：
Koziol, Agata;Grela, Ewa;Lochynski, Stanislaw
将贝克曼重排纳入本研究中导致了源自天然化合物的含氮萜类衍生物的形成。对起始单萜和所得衍生物的抗菌潜力进行了评估。在本研究中，金黄色葡萄球菌对所检测的化合物最敏感。对金黄色葡萄球菌进行的最低抑菌浓度（MIC）实验表明，（-）-薄荷酮肟（-）-8和（+）-胡薄荷酮肟（+）-13在测试的衍生物和起始化合物中具有最佳的抗菌活性。它们的 MIC90 值为 100 μg/mL。还评估了所得衍生物对细菌脲酶的抑制活性。在测试的化合物中，发现了三种活性抑制剂——肟14和内酰胺(-)-15和16限制巴氏孢子八菌脲酶的活性，K-i值分别为174.3μM、43.0μM和4.6μM。据我们所知，衍生物 16 是迄今为止描述的最活跃的抗尿素分解内酰胺。
Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (-)-menthone oxime (-)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 mu g/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found - oxime 14 and lactams (-)-15 and 16 limited the activity of Sporosarcina pasteurii urease with K-i values of 174.3 mu M, 43.0 mu M and 4.6 mu M, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.