Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives.
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.
Hamad
Nawar S
NS
Chemistry Department, College of Science, University of Basrah, Iraq.
Al-Haidery
Nahed H
NH
Al-Masoudi
Iman A
IA
Sabri
Mey
M
Sabri
Luma
L
Al-Masoudi
Najim A
NA
D000596:Amino Acids / Q000737:chemistry* / Q000494:pharmacology*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000596:Amino Acids; D019380:Anti-HIV Agents; D009281:Naphthalenes