Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic.
Department of Biological and Biochemical Sciences, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic.
Molecules. 2014 May 30;19(6):7152-68. doi: 10.3390/molecules19067152.
A new series of 27 diethyl 2-(phenylcarbamoyl)phenyl phosphorothioates (thiophosphates) was synthesized, characterized by NMR, IR and CHN analyses and evaluated against Mycobacterium tuberculosis H37Rv, Mycobacterium avium and two strains of Mycobacterium kansasii. The best activity against M. tuberculosis was found for O-{4-bromo-2-[(3,4-dichlorophenyl)carbamoyl]phenyl} O,O-diethyl phosphorothioate (minimum inhibitory concentration of 4 µM). The highest activity against nontuberculous mycobacteria was exhibited by O-(5-chloro-2-{[4-(trifluoromethyl)phenyl]carbamoyl}-phenyl) O,O-diethyl phosphorothioate with MIC values from 16 µM. Prepared thiophosphates were also evaluated against acetylcholinesterase from electric eel and butyrylcholinesterase from equine serum. Their inhibitory activity was compared to that of the known cholinesterases inhibitors galanthamine and rivastigmine. All tested compounds showed a higher (for AChE inhibition) and comparable (for BChE inhibition) activity to that of rivastigmine, with IC50s within the 8.04 to 20.2 µM range.
合成了一系列新的 27 种二乙基 2-（苯甲酰基）苯基硫代磷酸酯（硫代磷酸酯），通过 NMR、IR 和 CHN 分析进行了表征，并针对结核分枝杆菌 H37Rv、鸟分枝杆菌和两种堪萨斯分枝杆菌进行了评估。对结核分枝杆菌活性最高的是 O-{4-溴-2-[(3,4-二氯苯基)氨基甲酰基]苯基} O,O-二乙基硫代磷酸酯（最小抑菌浓度为 4 µM）。对非结核分枝杆菌活性最高的是 O-(5-氯-2-{[4-(三氟甲基)苯基]氨基甲酰基}苯基) O,O-二乙基硫代磷酸酯，MIC 值为 16 µM。还评估了制备的硫代磷酸酯对电鳗乙酰胆碱酯酶和马血清丁酰胆碱酯酶的抑制活性。将它们的抑制活性与已知的胆碱酯酶抑制剂加兰他敏和利伐斯的明进行了比较。所有测试的化合物对 AChE 的抑制活性均高于（对于 AChE 抑制）和可比（对于 BChE 抑制）利伐斯的明，IC50 范围在 8.04 至 20.2 µM 之间。
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