Synthesis of Pyrryl Aryl Sulfones Targeted at the HIV‐1 Reverse Transcriptase

Artico, M.; Silvestri, Romano; Stefancich, G.; Massa, S.; Pagnozzi, E.; Musu, D; Scintu, Francesco; Pinna, Elisabetta; Tinti, Elisa; Colla, Paolo La

doi:10.1002/ardp.19953280304

Cited by 32 publications

(21 citation statements)

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“…n Pyrrylarylsulfones Studies on diarylsulfone analogs led to the discovery of pyrrylarylsulfone (PAS) (6, 7) HIV-1 NNRTI class (table 1). Both the 2-nitrophenyl and 2-ethoxycarbonyl-1H-pyrrole groups were key requirements of first generation PAS [31]. The development of PAS NNRTI class considerably advanced by replacing the 2-nitrobenzene group with a para-chloroanilino moiety to provide a new generation of amino-PAS (7) endowed with potent antiviral activity at micromolar concentrations [32,33,101,102].…”

Section: Diarylsulfonesmentioning

confidence: 99%

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

et al. 2013

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HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) represent one of the most significant classes of drugs for the treatment of AIDS/HIV infection. Over the past two decades several potent arylsulfone-based HIV-1 NNRTIs and related analogs have been developed. This review provides an essential overview of the structure-activity relationships of the arylsulfone-based HIV-1 NNRTIs. Furthermore, structural information useful for the design and development of new sulfur containing NNRTIs with enhanced antiretroviral activity against HIV-1 wild type and clinically relevant drug resistant HIV-1 mutant strains will be discussed.

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Section: Diarylsulfonesmentioning

confidence: 99%

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

et al. 2013

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“…The most active compound, the dinitro derivative (2) (EC 50 = 0.89 µM), was discarded due to its poor bioavailability, whereas the (4-methoxy-2-nitrophenyl)phenylsulphone (3) (EC 50 = 3.4 µM) was selected for further studies. Artico et al [31] selected NPPS (1) as a lead compound for the design of new isosteres characterised by the presence of a pyrrole nucleus. The new pyrryl aryl sulphones (PAS) were less potent than NPPS, although they were also less cytotoxic (PAS, 4; EC 50 = 15.08 µM, CC 50 = > 308 µM).…”

Section: Towards the Design Of New Indolyl Aryl Sulphonesmentioning

confidence: 99%

Indolyl aryl sulphones as HIV-1 reverse transcriptase inhibitors: docking and 3D QSAR studies

Ragno

Coluccia

Regina

et al. 2007

Expert Opinion on Drug Discovery

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Indolyl aryl sulphones (IASs) are a potent class of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) developed from early studies on pyrryl aryl sulphones and pyrrolobenzothiadiazepines and correlated with Merck's compound L-737,126. This review focuses on how molecular modelling studies, refined structure-based drug design (SBDD) and ligand-based drug design (LBDD) guided the activity prediction, synthesis and biological evaluation of new potent and selective IASs. In particular, the binding mode analysis (SBDD) and three-dimensional quantitative structure-activity relationship (3D QSAR) models (LBDD) are discussed, and their use is elucidated in design projects. Both SBDD and LBDD studies have led to the disclosure of subnanomolar active compounds. These compounds are revealed to be active against the most clinically relevant HIV-1 mutant strains and some drug-resistant clinical-isolated strains.

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“…The presence of the nitro group at position 2 of the phenyl ring and the sulfur bridging atom as sulfur dioxide are fundamental structural characteristics for their activity. The antiviral activity of 2-nitrophenyl phenyl sulfone ( 50 , NPPS) [ 52 ] prompted the synthesis of a series of 41 pyrryl aryl sulfones (PAS) and some related derivatives [ 53 ]. Pyrryl 2-nitrophenyl sulfone ( 51 ) was straightforwardly prepared by nucleophilic substitution reaction between 2-nitrobenzenesulfonyl chloride and pyrrole in the presence of n -tetrabutylammonium hydrogen sulfate (TBAS) as a phase transfer catalyst.…”

Section: Pyrryl Aryl Sulfonesmentioning

confidence: 99%

N-Pyrrylarylsulfones with High Therapeutic Potential

2017

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This review illustrates the various studies made to investigate the activity of N-pyrrylarylsulfone containing compounds as potential antiviral, anticancer and SNC drugs. A number of synthetic approaches to obtain tetracyclic, tricyclic and non-cyclic compounds, and their biological activity with regard to structure–activity relationships (SARs) have been reviewed. The literature reviewed here may provide useful information on the potential of N-pyrrylarylsulfone pharmacophore as well as suggest concepts for the design and synthesis of new N-pyrrylarylsulfone based agents.

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Synthesis of Pyrryl Aryl Sulfones Targeted at the HIV‐1 Reverse Transcriptase

Cited by 32 publications

References 14 publications

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

Arylsulfone-Based HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors

Indolyl aryl sulphones as HIV-1 reverse transcriptase inhibitors: docking and 3D QSAR studies

N-Pyrrylarylsulfones with High Therapeutic Potential

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