Synthesis, characterization, structures and antioxidant activity of nicotinoyl based organoselenium compounds

Prabhu, C.; Phadnis, Prasad P.; Wadawale, Amey; Priyadarsini, K. Indira; Jain, Vimal K.

doi:10.1016/j.jorganchem.2012.04.014

Cited by 59 publications

(2 citation statements)

References 53 publications

(49 reference statements)

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“…The nicotinoyl derivative 3 was prepared from 12 , in turn obtained from 2-chloronicotinic acid by reaction with a freshly prepared ethanolic solution of Na 2 Se 2 . The target diselenide was obtained in high yield without any further purification.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity

et al. 2015

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The interest in the synthesis of Se-containing compounds is growing with the discovery of derivatives exhibiting various biological activities. In this manuscript, we have identified a series of 2,2'-diselenobisbenzamides (DISeBAs) as novel HIV retroviral nucleocapsid protein 7 (NCp7) inhibitors. Because of its pleiotropic functions in the whole viral life cycle and its mutation intolerant nature, NCp7 represents a target of great interest which is not reached by any anti-HIV agent in clinical use. Using the diselenobisbenzoic scaffold, amino acid, and benzenesulfonamide derivatives were prepared and biologically profiled against different models of HIV infection. The incorporation of amino acids such as glycine and glutamate into DISeBAs 7 and 8 resulted in selective anti-HIV activity against both acutely and chronically infected cells as well as an interesting virucidal effect. DISeBAs demonstrated broad antiretroviral activity, encompassing HIV-1 drug-resistant strains including clinical isolates, as well as simian immunodeficiency virus (SIV). Time of addition experiments, along with the observed dose dependent inhibition of the Gag precursor proper processing, confirmed that their mechanism of action is based on NCp7 inhibition.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity

et al. 2015

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“…From a view point of drug design for antioxidant therapy, much effort has been directed for decades toward development of organoselenium compounds [ 2 , 3 , 4 , 5 , 6 , 7 ], which can act as GPx-like catalysts, and also toward elucidation of their catalytic mechanisms [ 8 , 9 , 10 , 11 ]. Various GPx model compounds, most of which are aromatic diselenides (ArSeSeAr), have been developed and their catalytic activities have been evaluated [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. In the meantime, aliphatic and/or aromatic monoselenides (RSeR′) are also known to act as GPx-like catalysts through a unique selenide/selenoxide redox cycle ( Scheme 1 , cycle A), in which selenide 1 is oxidized by H 2 O 2 to the corresponding selenoxide 2 , which is reduced back to 1 by a thiol substrate (RSH) [ 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Glutathione Peroxidase-Like Activity of Amino-Substituted Water-Soluble Cyclic Selenides: A Shift of the Major Catalytic Cycle in Methanol

et al. 2017

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We previously reported that water-soluble cyclic selenides can mimic the antioxidative function of glutathione peroxidase (GPx) in water through a simple catalytic cycle, in which the selenide (>Se) is oxidized by H2O2 to the selenoxide (>Se=O) and the selenoxide is reduced by a thiol back to the selenide. In methanol, however, the GPx-like activity could not be explained by this simple scenario. To look into the reasons for the unusual behaviors in methanol, monoamino-substituted cyclic selenides with a variable ring size were synthesized, and the intermediates of the catalytic cycle were characterized by means of 77Se-NMR and LC–MS spectroscopies. In water, it was confirmed that the selenide and the selenoxide mainly contribute to the antioxidative function, though a slight contribution from the dihydroxy selenane (>Se(OH)2) was also suggested. In methanol, on the other hand, other active species, such as hydroxyselenonium (>Se+–OH) and hydroxy perhydroxy selenane (>Se(OH)(OOH)), could be generated to build another catalytic cycle. This over-oxidation would be more feasible for amino-substituted cyclic selenides, probably because the ammonium (NH3+) group would transfer a proton to the selenoxide moiety to produce a hydroxyselenonium species in the absence of an additional proton source. Thus, a shift of the major catalytic cycle in methanol would make the GPx-like antioxidative function of selenides perplexing.

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Visible‐Light‐Induced Difunctionalization of Styrenes: An Efficient and Green Protocol for the Synthesis of β‐Acyloxyselenides

Chen

Mei

et al. 2020

Asian J Org Chem

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An efficient and green protocol for synthesizing β‐acyloxyselenides was developed through the visible‐light‐induced difunctionalization of styrenes with a binary system of diaryldiselenides and carboxylic acids under mild reaction conditions, without using any transition‐metal‐catalysts. This protocol is scalable and tolerates a wide spectrum of styrenes and carboxylic acids to deliver the corresponding products in moderate to excellent yields, providing convenient approach to β‐acyloxyselenides.

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Synthesis, characterization, structures and antioxidant activity of nicotinoyl based organoselenium compounds

Cited by 59 publications

References 53 publications

Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity

Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity

Glutathione Peroxidase-Like Activity of Amino-Substituted Water-Soluble Cyclic Selenides: A Shift of the Major Catalytic Cycle in Methanol

Visible‐Light‐Induced Difunctionalization of Styrenes: An Efficient and Green Protocol for the Synthesis of β‐Acyloxyselenides

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