Ateş O, Kocabalkanli A, Saniş G O, Ekinci A C, Vidin A
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Istanbul. Turkey.
Arzneimittelforschung. 1997 Oct;47(10):1134-8.
Reaction of 5-aryl-2-amino-1,3,4-oxadiazoles (BI-VI), obtained by the oxydative cyclization of aromatic aldehyde semicarbazones (AI-VI), with alpha-chloro-alpha-phenylacetyl chloride and alpha-bromopropionyl bromide yielded 5-aryl-2-[(alpha-chloro-alpha-phenylacetyl)amino]-1,3,4-oxadiazoles (Ia-VIa) and 5-aryl-2-[(alpha-bromopropionyl)amino]-1,3,4-oxadiazoles (VIIa-XIIa), respectively. Furthermore, Ia-XIIa were refluxed with ammonium thiocyanate to give 5-phenyl/methyl-2-[(5-aryl-1,3,4-oxadiazol-2-yl)imino]-4-thiazo lidinones (It-XIIt). All compounds were tested for antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa. They were all found to possess significant activity against S. aureus with MIC values ranging from 0.24 to 125 micrograms/ml. LD50 of compounds chosen as prototypes are estimated.
由芳族醛缩氨基脲(AI-VI)氧化环化得到的5-芳基-2-氨基-1,3,4-恶二唑(BI-VI)与α-氯-α-苯基乙酰氯和α-溴丙酰溴反应,分别生成5-芳基-2-[(α-氯-α-苯基乙酰基)氨基]-1,3,4-恶二唑(Ia-VIa)和5-芳基-2-[(α-溴丙酰基)氨基]-1,3,4-恶二唑(VIIa-XIIa)。此外,将Ia-XIIa与硫氰酸铵回流,得到5-苯基/甲基-2-[(5-芳基-1,3,4-恶二唑-2-基)亚氨基]-4-噻唑烷酮(It-XIIt)。测试了所有化合物对金黄色葡萄球菌、大肠杆菌、肺炎克雷伯菌和铜绿假单胞菌的抗菌活性。发现它们对金黄色葡萄球菌均具有显著活性,MIC值范围为0.24至125微克/毫升。估计了选为原型的化合物的半数致死量(LD50)。