PDF(Pubmed)
Abstract：
The chemical reaction of 2-(methylsulfinyl)naphtho[2,3-d]thiazole-4,9-dione (3) using different amines, including benzylamine (4a), morpholine (4b), thiomorpholine (4c), piperidine (4d), and 4-methylpiperazine (4e), produced corresponding new tricyclic naphtho[2,3-d]thiazole-4,9-dione compounds (5a-e) in moderate-to-good yields. The photophysical properties and antimicrobial activities of these compounds (5a-e) were then characterized. Owing to the extended π-conjugated system of naphtho[2,3-d]thiazole-4,9-dione skeleton and substituent effect, 5a-e showed fluorescence both in solution and in the solid state. The introduction of nitrogen-containing heterocycles at position 2 of the thiazole ring on naphtho[2,3-d]thiazole-4,9-dione led to large bathochromic shifts in solution, and 5b-e exhibited orange-red fluorescence with emission maxima of over 600 nm in highly polar solvents. Staphylococcus aureus (S. aureus) is a highly pathogenic bacterium, and infection with its antimicrobial-resistant pathogen methicillin-resistant S. aureus (MRSA) results in serious clinical problems. In this study, we also investigated the antimicrobial activities of 5a-e against S. aureus, MRSA, and S. epidermidis. Compounds 5c with thiomorpholine group and 5e with 4-methylpiperazine group showed potent antimicrobial activity against these bacteria. These results will lead to the development of new fluorescent dyes with antimicrobial activity in the future.
摘要：
2-（甲基亚磺酰基）萘并[2,3-d]噻唑-4,9-二酮（3）使用不同胺的化学反应，包括苄胺(4a)，吗啉(4b)，硫代吗啉(4c)，哌啶(4d),和4-甲基哌嗪(4e)，以中等至良好的收率产生相应的新的三环萘并[2,3-d]噻唑-4,9-二酮化合物（5a-e）。然后表征这些化合物(5a-e)的光物理性质和抗微生物活性。由于萘并[2,3-d]噻唑-4,9-二酮骨架的扩展π-共轭体系和取代基效应，图5a-e在溶液和固态中均显示荧光。在萘并[2,3-d]噻唑-4,9-二酮上噻唑环的2位引入含氮杂环导致溶液中的红移大，和5b-e在高极性溶剂中表现出橙红色荧光，发射最大值超过600nm。金黄色葡萄球菌（S。金黄色葡萄球菌）是一种高致病性细菌，和其抗菌素耐药病原体耐甲氧西林金黄色葡萄球菌（MRSA）的感染导致严重的临床问题。在这项研究中,我们还研究了5a-e对金黄色葡萄球菌的抗菌活性，MRSA,和表皮葡萄球菌。具有硫代吗啉基团的化合物5c和具有4-甲基哌嗪基团的化合物5e对这些细菌显示出有效的抗微生物活性。这些结果将导致未来具有抗菌活性的新型荧光染料的开发。
