Chemistry Department, College of Science, University of Basrah, Iraq.
Arch Pharm (Weinheim). 2010 Jul;343(7):397-403. doi: 10.1002/ardp.200900293.
A new series of 2-(naphthalen-2-yloxy)-N-[(aryl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl] acetamides 5a-f was synthesized from naphthalene-derived glycine derivative 2 via the hydrazinoacetamide analogs 4a-f. Alternatively, treatment of 4a with H(2)SO(4) afforded 2-(naphthalen-2-yloxy)-N-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)methyl) acetamide 6a. Alkylation or sulphonylation of 5a afforded the S-alkylated derivatives 7 and 8, respectively. Interestingly, treatment of 3 with methoxide ion gave the triazine derivative 9. The synthesized compounds have been screened for their inhibitory activity against HIV-1 and HIV-2 in MT-4 cells. However, 7 was found to be the potent inhibitor in vitro for the replication of HIV-1 (EC(50 )= 0.20 microg/mL), suggesting a new lead in the development of an antiviral agent.
合成了一系列新的 2-（萘-2-氧基）-N-[(芳基-5-硫代-4,5-二氢-1H-1,2,4-三唑-3-基)甲基]乙酰胺 5a-f，该系列化合物是由萘衍生的甘氨酸衍生物 2 通过肼基乙酰胺类似物 4a-f 得到的。或者，用 H(2)SO(4)处理 4a 得到 2-（萘-2-氧基）-N-((5-(苯氨基)-1,3,4-噻二唑-2-基)甲基)乙酰胺 6a。5a 的烷基化或磺化分别得到 S-烷基化衍生物 7 和 8。有趣的是，用甲氧基离子处理 3 得到三嗪衍生物 9。对合成的化合物进行了抗 HIV-1 和 HIV-2 在 MT-4 细胞中的抑制活性筛选。然而，7 被发现是体外抑制 HIV-1 复制的有效抑制剂（EC(50 )= 0.20 microg/mL），提示了一种新的抗病毒药物开发的先导化合物。
