Organylzinc Chalcogenolate Promoted Michael‐Type Addition of α,β‐Unsaturated Carbonyl Compounds

Nunes, Vanessa Loren; Oliveira, Ingryd Cristina de; Barros, Olga Soares do Rego

doi:10.1002/ejoc.201301497

Cited by 17 publications

(3 citation statements)

References 32 publications

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“…With the general principle of bioisosterism in mind and considering the ability of selenium to coordinate bivalent zinc cations, , we decided to synthesize and evaluate the anti-HIV activity of a series of 2,2′-diselenobisbenzamides (DISeBAs).…”

Section: Introductionmentioning

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: Introductionmentioning

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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“…Additionally, zinc organoselenolate, prepared by the cleavage of diorganyl diselenide with a zinc dust/NH 4 OH system, can also act as a nucleophile to promote the reduction of alkynes leading to the formation of 166 vinyl selenides (Scheme 158). [228] In this methodology, the Z ‐vinylic selenides were predominantly formed via an anti‐Markovnikov addition of the organylselenolate across the triple bond. A biphasic system formed by elemental zinc, hydrochloric acid, and ethyl ether also effectively promoted the alkyne reduction to give predominantly Z ‐vinyl selenides [229] .…”

Section: Diorganyl Diselenides Promoting Reduction Of Alkynesmentioning

confidence: 99%

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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Diorganyl diselenides have emerged as privileged structures because they are easy to prepare, have distinct reactivity, and have broad biological activity. They have also been used in the synthesis of natural products as an electrophile in the organoselenylation of aromatic systems and peptides, reductions of alkenes, and nucleophilic substitution. This review summarizes the advancements in methods for the transformations promoted by diorganyl diselenides in the main functions of organic chemistry. Parallel, it will also describe the main findings on pharmacology and toxicology of diorganyl diselenides, emphasizing anti‐inflammatory, hypoglycemic, chemotherapeutic, and antimicrobial activities. Therefore, an examination detailing the reactivity and biological characteristics of diorganyl diselenides provides valuable insights for academic researchers and industrial professionals.

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“…In order to obtain nucleophilic selenium species, we became interested in the applicability of zinc. The use of this metal in the S-S and Se-Se bond cleavages was already described, in combination with Lewis acids, such as aluminum chloride (AlCl 3 ) [40,41], zirconium tetrachloride (ZrCl 4 ) [42], RuCl 3 [43] and TiCl 4 [44], or simply basic [45] or acidic conditions [46]. The zinc insertion into Se-Halogen bond leading to the umpolung of the selenium atom and the formation of the first class of bench stable zinc selenolates, was deeply investigated, with a broad synthetic applicability [47][48][49][50][51][52][53][54][55].…”

Section: Introductionmentioning

confidence: 99%

A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors

et al. 2020

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In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic α,β-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive β-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, α,β-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7° recycling rounds).

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Organylzinc Chalcogenolate Promoted Michael‐Type Addition of α,β‐Unsaturated Carbonyl Compounds

Cited by 17 publications

References 32 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

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors

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