Anti-HIV activity of stilbene-related heterocyclic compounds

Bedoya, Luis Miguel; Olmo, Esther del; Sancho, Rocı́o; Barboza, Bianca; Beltrán, Manuela; García-Cadenas, Ana Esther; Sánchez-Palomino, Sonsoles; López-Pérez, Jose Luis; Muñóz, Eduardo; Feliciano, Arturo San; Alcamı́, José

doi:10.1016/j.bmcl.2006.04.087

Cited by 48 publications

(21 citation statements)

References 21 publications

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“…Though benzodiazepine derivatives were not successful in terms of selectivity for Tat and activity in patients, the screening of small molecule inhibitors against Tat gave the first example that they can inhibit transcription in some types of acutely, chronically and latently HIV infected cell lines. Therefore, several other studies have used LTR-reporter assays to find Tat-dependent transcription inhibitors such as keto/enol epoxy steroids [157], purine derivatives [158,159], tanic acids [160], D-penicillamin [161,162], organic thiophosphate WR-151327 [163], b-carbolines [139,140], camptothecin [144,164], durhamycin A [165], monocyclin IV [166], 3-phenylcoumarins and chalcones [167], stilbene related heterocyclic compounds [168], 4-phenylcoumarins and derivatives (both anti NF-kB and Tat activities) [169], topotecan, b-lapachome, [144], toco-pheryl curcumin (C3) [170], the cyclopentanone prostaglandin PGJ 2 [171,172], celasterol [173], bis-anthracycline antibiotics (WP 631; a DNA intercalator) [137], the natural product EM2487 [174], thiamine disulfide [175] and 2-glycineamide-5-chlorophenyl-2-pyril ketone [176]. Recently, Chande et al .…”

Section: Small Molecules Inhibitors Of Hiv Transcriptionmentioning

confidence: 99%

Strategies to Block HIV Transcription: Focus on Small Molecule Tat Inhibitors

Mousseau

Valente

2012

Biology

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After entry into the target cell, the human immunodeficiency virus type I (HIV) integrates into the host genome and becomes a proviral eukaryotic transcriptional unit. Transcriptional regulation of provirus gene expression is critical for HIV replication. Basal transcription from the integrated HIV promoter is very low in the absence of the HIV transactivator of transcription (Tat) protein and is solely dependent on cellular transcription factors. The 5' terminal region (+1 to +59) of all HIV mRNAs forms an identical stem-bulge-loop structure called the Transactivation Responsive (TAR) element. Once Tat is made, it binds to TAR and drastically activates transcription from the HIV LTR promoter. Mutations in either the Tat protein or TAR sequence usually affect HIV replication, indicating a strong requirement for their conservation. The necessity of the Tat-mediated transactivation cascade for robust HIV replication renders Tat one of the most desirable targets for transcriptional therapy against HIV replication. Screening based on inhibition of the Tat-TAR interaction has identified a number of potential compounds, but none of them are currently used as therapeutics, partly because these agents are not easily delivered for an efficient therapy, emphasizing the need for small molecule compounds. Here we will give an overview of the different strategies used to inhibit HIV transcription and review the current repertoire of small molecular weight compounds that target HIV transcription.

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Section: Small Molecules Inhibitors Of Hiv Transcriptionmentioning

confidence: 99%

Strategies to Block HIV Transcription: Focus on Small Molecule Tat Inhibitors

Mousseau

Valente

2012

Biology

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“…It has been found that some of derivatives of phthalazinones exhibit potent inhibition of phosphodiesterase (PDE4) activity [11] and agonist activity to dopamine D 2 and serotonin 5-HT 2 receptors [12]. The research studies of the last years also show that a few of the analogues of phthalazinones inhibit HIV replication [13].…”

Section: Introductionmentioning

confidence: 97%

Synthesis and Pharmacological Evaluation of N‐(Dimethylamino)ethyl Derivatives of Benzo‐ and Pyridopyridazinones

Pakulska

Malinowski

Szcześniak

et al. 2008

Archiv der Pharmazie

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New N-(dimethylamino)ethyl derivatives of phthalazinones and pyridopyridazinones 7, 9 were synthesized and assayed as potential analgesic agents in the hot-plate, tail-flick, and writhing tests. Pharmacological assay demonstrated that eight (in ten) of the newly synthesized compounds showed antinociceptive activity. Especially, 2-[2-(dimethylamino)ethyl]-4-phenyl-2H-phthalazin-1-one 7a showed remarkably higher antinociceptive activity in all tests. This is connected with influence on supraspinal, spinal, and peripheral structures. The decreased sensitivity to the pain stimulus in the hot-plate was higher than that of metamizole.

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“…1 Its unique biological activities serving as anti-convulsant, 2 anti-microbial, 3 antifungal, 4 vasorelaxant, 5 anti-HIV, 6 anti-cancer activity, 7 PDE3/PDE4 inhibitory agents, 8 anti-asthamatic, 9 leishmanicidal 10 and anti-diabetic have made synthetic studies of the phthalazine ring system attractive over the years. The chemical oxidation of 2,3-dihydrophthalazine-1,4-dione and its derivatives has previously been carried out both in water and organic solvents for the synthesis of some organic compounds via the nucleophilic addition or Diels-Alder reactions.…”

Section: Introductionmentioning

confidence: 99%

Oxidative ring cleavage of 2,3-dihydrophthalazine-1,4-dione in aqueous and non-aqueous solutions: Electrochemical and kinetic studies

et al. 2014

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Electrochemical oxidation of 2,3-dihydrophthalazine-1,4-dione (DHP) has been investigated in aqueous and some amphiprotic and aprotic non-aqueous solvents by cyclic voltammetric and controlledpotential coulometric techniques. Our data shows that electrochemically generated phthalazine-1,4-dione (PTD) in water and amphiprotic non-aqueous solvents participates in an oxidative ring cleavage (ORC) reaction to form phthalic acid. The rate of this reaction is dependent. On autoprotolysis constant (K SH ) and basicity of the solvent. Therefore, in the aprotic non-aqueous solvents such as acetonitrile and DMSO, the rate of ORC is too slow to be observed on the time-scale of cyclic voltammetry.

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Anti-HIV activity of stilbene-related heterocyclic compounds

Cited by 48 publications

References 21 publications

Strategies to Block HIV Transcription: Focus on Small Molecule Tat Inhibitors

Strategies to Block HIV Transcription: Focus on Small Molecule Tat Inhibitors

Synthesis and Pharmacological Evaluation of N‐(Dimethylamino)ethyl Derivatives of Benzo‐ and Pyridopyridazinones

Oxidative ring cleavage of 2,3-dihydrophthalazine-1,4-dione in aqueous and non-aqueous solutions: Electrochemical and kinetic studies

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