Akbari Dilmaghani Karim, Nasuhi Pur Fazel, Hatami Nezhad Mahnaz
Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran.
Health Technology Incubator Center, Urmia University of Medical Science, Urmia, Iran.
Iran J Pharm Res. 2015 Summer;14(3):693-9.
The condensation reaction of 5-(4-aminophenyl)-4-phenyl-1,2,4-triazole-3-thione with salicylaldehyde, 4-hydroxybenzaldehyde, 5-chlorosalicylaldehyde, 5-bromosalicylaldehyde, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde and 4-methoxybenzaldehyde in methanol results in series of new Schiff bases. The structure of Schiff bases were confirmed by (1)H NMR, (13)C NMR, IR and mass spectroscopy. The synthesized compounds were tested for their antimicrobial activity against bacterial (Gram negative and Gram positive) strains in-vitro. The synthetic compounds showed different inhibition zones against tested bacterial strains. All compounds showed significant antiproliferative activity against Acinetobacter calcoaceticus ATCC 23055. In detail, Entrococcus faecalis (Gram positive) was resistant to all prepared compounds, whereas, A. calcoaceticus (Gram negative) was sensitive to all compounds especially 5c, 5d and 4. S. aureus (Gram positive, relatively resistant to antimicrobials) showed limited sensitivity to only 5c and 5d, and it was resistant to all other compounds and only 5c exhibited low activity against P. aeruginosa (Gram negative). The best results belonged to 5c that showed high activity against A. calcoaceticus (33 mm) as well as S. aureus (20 mm).
5-(4-氨基苯基)-4-苯基-1,2,4-三唑-3-硫酮与水杨醛、4-羟基苯甲醛、5-氯水杨醛、5-溴水杨醛、2-硝基苯甲醛、3-硝基苯甲醛、4-硝基苯甲醛和4-甲氧基苯甲醛在甲醇中发生缩合反应，生成了一系列新的席夫碱。通过¹H NMR、¹³C NMR、红外光谱和质谱对席夫碱的结构进行了确认。对合成的化合物进行了体外抗细菌（革兰氏阴性和革兰氏阳性）菌株的抗菌活性测试。合成的化合物对测试的细菌菌株显示出不同的抑菌圈。所有化合物对醋酸钙不动杆菌ATCC 23055均表现出显著的抗增殖活性。具体而言，粪肠球菌（革兰氏阳性）对所有制备的化合物均有抗性，而醋酸钙不动杆菌（革兰氏阴性）对所有化合物均敏感，尤其是5c、5d和4。金黄色葡萄球菌（革兰氏阳性，对抗菌剂相对耐药）仅对5c和5d表现出有限的敏感性，对所有其他化合物均有抗性，且只有5c对铜绿假单胞菌（革兰氏阴性）表现出低活性。最佳结果属于5c，它对醋酸钙不动杆菌（33毫米）和金黄色葡萄球菌（20毫米）均表现出高活性。
