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Amino Acid Derivatives, Part 4: Synthesis and Anti -HIV Activity of New Naphthalene Derivatives

Authors:
Nawar S Hamad
Nawar S Hamad
Nawar S Hamad
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Nahed al Haidery at University of Basrah
Nahed al Haidery
Iman A Al-Masoudi
Iman A Al-Masoudi
Iman A Al-Masoudi
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Mey Sabri
Mey Sabri
Mey Sabri
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Abstract

Amino Acid Derivatives, Part 4: Synthesis and Anti‐HIV Activity of New Naphthalene Derivatives Authors Nawar S Hamad, Nahed H Al‐Haidery, Iman A Al‐Masoudi, Mey Sabri, Luma Sabri, Najim A Al‐Masoudi Publication date 2010/7 Journal Archiv der Pharmazie Volume 343 Issue 7 Pages 397-403 Publisher WILEY‐VCH Verlag Description 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. Total citations Cited by 18 2012201320142015201620172018 Scholar articles Amino Acid Derivatives, Part 4: Synthesis and Anti‐HIV Activity of New Naphthalene Derivatives NS Hamad, NH Al‐Haidery, IA Al‐Masoudi, M Sabri… - Archiv der Pharmazie, 2010 Cited by 18 Related articles All 7 versions
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Arch Pharm (Weinheim). 2010 Jul;343(7):397-403. doi: 10.1002/ardp.200900293.
Amino acid derivatives, part 4: synthesis
and anti-HIV activity of new naphthalene
derivatives.
Hamad NS1, Al-Haidery NH, Al-Masoudi IA, Sabri M, Sabri L, Al-Masoudi NA.
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 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.
PMID:
20379971
[PubMed - indexed for MEDLINE]
... Thiadiazole is a widely-known and significant heterocyclic compound found in numerous natural and pharmaceutical products. Thiadiazole derivatives are considered as the main component of most drugs, such as antimicrobial [9], antiinflammatory [10], antiviral [11], anticancer [13], antioxidant [12], antibacterial [14], anticonvulsant [15], antileishmanial [17], antitumor [16], as well as antifungal agent [18]. Based on this core, the present study evaluates the structural changes that have been made of multiple thiadiazole derivatives for various pharmacological activities. ...
... This intermediate was then combined with various substituted benzaldehyde into ethanol with the addition of triethylamine under reflux for about 6 hours to produce thiadiazole-bearig Schiff base derivatives. (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). All fresh products were extracted after six hours at low pressure after solvent evaporation. ...
... Thiadiazole derivatives were synthesized in two steps with Schiff base moiety (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). Thiosemicarbazide (1 equivalent) was added to 2-trifluoro-5-chlorobenzaldehyde (1 equivalent) in 1,4-dioxne (10 mL) along with potassium carbonate to afford an intermediate (II), the mixture was refluxed for 3 hours. ...
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