Antipenko Lyudmila, Karpenko Alexander, Kovalenko Sergey, Katsev Andrew, Komarovska-Porokhnyavets Elena, Novikov Vladimir, Chekotilo Aleksey
Department of Pharmaceutical Chemistry, Zaporozhye State Medical University, 69035 Zaporozhye, Ukraine.
Chem Pharm Bull (Tokyo). 2009 Jun;57(6):580-5. doi: 10.1248/cpb.57.580.
A series of novel ([1,2,4]triazolo[1,5-c]quinazolin-2-ylthio)carboxylic acids 2a-d and esters 3a-l were synthesized and evaluated for antimicrobial activity. Alkylation of potassium 2-thio-[1,2,4]triazolo[1,5-c]quinazoline 1 with halogenocarboxylic acids and its esters proceeded S-regioselectively. During acid catalyzed esterification of 2a-c, degradation of the pyrimidine ring was observed. The structures of the compounds were elucidated by FT-IR, (1)H- and (13)C-NMR, electron impact mass spectra (EI-MS) and LC-MS spectral data. Antimicrobial and antifungal activity of synthesized compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Aspergillus niger, Mycobacterium luteum, Candida albicans and Candida tenuis. Acids 2a and 2c exhibited significant activity against C. albicans, which was additionally confirmed by the bioluminescence inhibition test and interrelated with their lipophilicity.
合成了一系列新型的([1,2,4]三唑并[1,5 - c]喹唑啉 - 2 - 硫基)羧酸2a - d和酯3a - l，并对其抗菌活性进行了评估。2 - 硫基 - [1,2,4]三唑并[1,5 - c]喹唑啉钾1与卤代羧酸及其酯的烷基化反应具有S - 区域选择性。在2a - c的酸催化酯化过程中，观察到嘧啶环的降解。通过傅里叶变换红外光谱(FT - IR)、氢核磁共振(¹H - NMR)、碳核磁共振(¹³C - NMR)、电子轰击质谱(EI - MS)和液相色谱 - 质谱(LC - MS)光谱数据对化合物的结构进行了阐明。测试了合成化合物对大肠杆菌、铜绿假单胞菌、黑曲霉、藤黄分枝杆菌、白色念珠菌和季也蒙念珠菌的抗菌和抗真菌活性。酸2a和2c对白色念珠菌表现出显著活性，这通过生物发光抑制试验得到进一步证实，并与其亲脂性相关。
