Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives
| Autor: | Najim A. Al-Masoudi, Luma Sabri, Nahed H. Al-Haidery, Iman A. Al-Masoudi, Nawar S. Hamad, Mey Sabri |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Chemistry Stereochemistry Anti-HIV Agents Pharmaceutical Science Microbial Sensitivity Tests Alkylation Methoxide Naphthalenes In vitro Amino acid chemistry.chemical_compound Structure-Activity Relationship Drug Discovery Glycine Structure–activity relationship Amino Acids Acetamide Naphthalene |
| Zdroj: | Archiv der Pharmazie. 343(7) |
| ISSN: | 1521-4184 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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