新型喹唑啉-4-酮 1,2,3-三唑共轭物的合成与抗菌活性。
Synthesis and antimicrobial activity of novel 1,2,3-triazole-conjugates of quinazolin-4-ones.
机构信息
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Lodz, Poland.
Faculty of Pharmacy, Department of Pharmaceutical Microbiology and Microbiological Diagnostics, Medical University of Lodz, Lodz, Poland.
出版信息
Arch Pharm (Weinheim). 2019 Mar;352(3):e1800302. doi: 10.1002/ardp.201800302. Epub 2019 Jan 30.
A novel series of diethyl{4-[(4-oxoquinazolin-3(4H)-yl)methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates 9aa-aj and their respective derivatives substituted at C6 of the quinazolinone moiety with a bromine atom (9ba-bj) or a nitro group (9ca-cj) were synthesized and assessed for the antibacterial activity toward selected Gram-positive and Gram-negative bacteria. Their antifungal activity was also screened. Compound 9ac was found to be the most active against Staphylococcus aureus ATCC 6535 (MIC 0.625 mg/mL, MBC 1.25 mg/mL), phosphonates 9ab-ai showed promising activity against Enterococcus faecalis ATCC 29212 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL), while compounds 9ac-j appeared the most active toward Pseudomonas aeruginosa ATCC 27853 (MIC = 0.625 mg/mL, MBC = 1.25 mg/mL). Antifungal assays of compounds 9aa-aj, 9ba-bj, and 9ca-cj were conducted on Candida albicans ATCC 10231 and Aspergillus brasiliensis ATCC 16404 and revealed noticeable activity of 9aa-aj (MIC = 1.25 mg/mL).
一系列新型的二乙基{4-[(4-氧代喹唑啉-3(4H)-基)甲基]-1H-1,2,3-三唑-1-基}烷基膦酸酯 9aa-aj 及其各自的衍生物被合成，这些衍生物在喹唑啉酮部分的 C6 位上被溴原子（9ba-bj）或硝基取代（9ca-cj），并评估了它们对选定革兰氏阳性和革兰氏阴性细菌的抗菌活性。它们的抗真菌活性也进行了筛选。化合物 9ac 对金黄色葡萄球菌 ATCC 6535 的活性最高（MIC 0.625 mg/mL，MBC 1.25 mg/mL），膦酸酯 9ab-ai 对粪肠球菌 ATCC 29212 表现出良好的活性（MIC = 0.625 mg/mL，MBC = 1.25 mg/mL），而化合物 9ac-j 对铜绿假单胞菌 ATCC 27853 的活性最高（MIC = 0.625 mg/mL，MBC = 1.25 mg/mL）。对化合物 9aa-aj、9ba-bj 和 9ca-cj 进行了抗真菌试验，针对白色念珠菌 ATCC 10231 和巴西曲霉 ATCC 16404，发现 9aa-aj 具有显著的活性（MIC = 1.25 mg/mL）。
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