Amino Acid Derivatives,Part 4: Synthesis and Anti‐HIV Activity of New Naphthalene Derivatives |
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Authors: | Nawar S. Hamad Nahed H. Al‐Haidery Iman A. Al‐Masoudi Mey Sabri Luma Sabri Najim A. Al‐Masoudi |
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Affiliation: | 1. Chemistry Department, College of Science, University of Basrah, Iraq. Fax: +964 770 570‐0509 and +49 7531 34435;2. College of Veterinary, University of Basrah, Basrah, Iraq |
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Abstract: | 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 H2SO4 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 (EC50 = 0.20 μg/mL), suggesting a new lead in the development of an antiviral agent. |
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Keywords: | Amino acid derivatives Anti‐HIV activity 2‐Mercapto‐1,2,4‐triazole Naphthalene 1,3,4‐Thiadiazole |
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