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Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1

Identifieur interne : 000846 ( Istex/Curation ); précédent : 000845; suivant : 000847

Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1

Auteurs : Esra Tatar [Turquie] ; Lkay Küçükgüzel [Turquie] ; Dirk Daelemans [Belgique] ; Tanaji T. Talele [États-Unis] ; Neerja Kaushik-Basu [États-Unis] ; Erik De Clercq [Belgique] ; Christophe Pannecouque [Belgique]

Source :

Archiv der Pharmazie [ 0365-6233 ] ; 2013-02.

RBID : ISTEX:7F0B79C3003E6A746C16DD9A4FBEC596D1488B8D

English descriptors

Teeft :
- Acid hydrazide, Acylhydrazone, Acylhydrazones, Alkyl, Amide, Amino acid side chains, Anal, Antiviral, Antiviral activity, Assay, Biol, Bioorg, Calcd, Cell culture, Chem, Clercq, Compound, Crude product, Default parameters, Derivative, Dextran sulfate, Docking, Gmbh, Hplc, Hydrazide, Hydrazine hydrate, Hydrazone, Hydrazone derivatives, Hydrazones, Iiib, Iiib nnrtir, Information table, Inhibitor, Kgaa, Ltered, Marmara university, Moiety, Nnrti, Nnrti mode, Novel site, Online version, Petroleum ether, Pharm, Reaction medium, Stereoselective, Stereoselective inhibitors, Tatar, Test compound, Test compounds, Transcriptase, Verlag, Verlag gmbh, Weinheim, Weinheim arch, Weinheim hydrazones, Wild type.

Abstract

In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.

Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. 8 S, 11 S, and 12 S showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers 8R, 11R, and 12 R were inactive against HIV‐1 strain IIIB. Molecular docking calculations of the R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.

Url:

https://api.istex.fr/ark:/67375/WNG-XDF0L29D-B/fulltext.pdf

DOI: 10.1002/ardp.201200311

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<front><div type="abstract" xml:lang="en">In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti‐HIV‐1 activity with a 50% inhibitory concentration (IC50) = 123.8 µM (selectivity index, SI > 3), IC50 = 12.1 µM (SI > 29), IC50 = 17.4 µM (SI > 19), respectively. Enantiomers 8R, 11R, and 12R were inactive against the HIV‐1 strain IIIB. Hydrazones 8S, 11S, and 12S which were active against HIV‐1 wild type showed no inhibition against a double mutant NNRTI‐resistant strain (K103N;Y181C). Molecular docking calculations of R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</div>
<div type="abstract" xml:lang="en">Acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. 8 S, 11 S, and 12 S showed anti‐HIV‐1 activity with a 50% inhibitory concentration of 123.8, 12.1, and 17.4 µM, respectively. Enantiomers 8R, 11R, and 12 R were inactive against HIV‐1 strain IIIB. Molecular docking calculations of the R‐ and S‐enantiomers of 8, 11, and 12 were performed using the hydrazone‐bound novel site of HIV‐1 RT.</div>
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Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1

Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1

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English descriptors

Abstract

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