Organic Research Laboratory, Department of Chemistry, Veer Narmad South Gujarat University, Udhana-Magdalla Road, Surat 395 007, Gujarat, India.
Eur J Med Chem. 2013 Apr;62:677-87. doi: 10.1016/j.ejmech.2012.12.055. Epub 2013 Jan 23.
A novel series of 5-(2-benzylsulfanyl-pyridin-3-yl)-2-(substituted)-sulfanyl-1,3,4-oxadiazoles 6a-j were synthesized from key intermediate 5-(2-benzylsulfanyl-pyridin-3-yl)-3H-[1,3,4]oxadiazole-2-thione 5. Nucleophilic substitution reactions with different electrophiles (E+), such as haloacetate and haloalkyl groups, were performed to get target compounds 6a-j. Compounds were characterized by NMR, mass, IR spectra and C, H, N analyses. All compounds were evaluated for their antimicrobial and antimycobacterial activities; selected analogs were screened for their anticancer activity on 60 tumor cell lines at single dose 1.00(-5) M. Unfortunately, none of the compounds showed a significant antitumor activity on 60 human tumor cell lines. However, compounds 6g and 6f with benzothiazole moiety (12.5 and 25 μg/ml) showed promising activity against Escherichia coli compared to ampicillin; compounds 6d, 6j bearing triazole and morpholine, respectively, showed promising antitubercular activity (25 μg/ml) compared to rifampicin.
一种新型的 5-(2-苄基硫代-吡啶-3-基)-2-(取代)-硫代-1,3,4-恶二唑系列 6a-j 是由关键中间体 5-(2-苄基硫代-吡啶-3-基)-3H-[1,3,4]恶二唑-2-硫酮 5 合成的。用不同的亲电试剂（E+），如卤代乙酸酯和卤代烷基，进行亲核取代反应，得到目标化合物 6a-j。用 NMR、质谱、IR 光谱和 C、H、N 分析对化合物进行了表征。所有化合物均进行了抗菌和抗分枝杆菌活性评价；选择的类似物在单剂量 1.00(-5) M 下对 60 种肿瘤细胞系进行了抗癌活性筛选。不幸的是，没有一种化合物对 60 个人类肿瘤细胞系表现出显著的抗肿瘤活性。然而，带有苯并噻唑部分的化合物 6g 和 6f（12.5 和 25 μg/ml）对大肠杆菌的活性与氨苄西林相当；分别带有三唑和吗啉的化合物 6d、6j 对结核分枝杆菌的活性（25 μg/ml）与利福平相当。
