Targeting the GSTP-dependent control of cell kinases and apoptosis with PhSeZnCl: a new seleno-organic drug

Legnaioli, S.; Piroddi, Marta; Tidei, Caterina; Santi, Claudio; Galli, Francesco

doi:10.1016/j.freeradbiomed.2012.08.235

“…Some selenium-containing molecules can behave as antioxidants, enzyme mimics and inhibitors, immunomodulators, cytoprotectors, antitumoral, anti-inflammatory, antihypertensive, and anti-infective agents [13][14][15][16]. Additionally, we have reported on the immunomodulatory and cytotoxic properties of selenium-containing compounds and their activity as inhibitors of several different enzymes and proteins, such as glutathione transferase (GSTp) and NCp7, which indicate interesting potential applications in anticancer and anti-HIV chemotherapy [17,18].…”

Section: Introductionmentioning

confidence: 99%

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

Nacca

¹

,

Monti

²

,

Lenardão

³

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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Copper(I)‐Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α‐Substituted α,β‐Unsaturated Thioamides

Tian

¹

,

Zhang

²

,

Yin

³

2023

Angewandte Chemie

4

0

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Herein, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and αsubstituted α,β-unsaturated thioamides is disclosed, which affords a series of chiral selenides in high to excellent enantioselectivity. As for both selenols and αsubstituted α,β-unsaturated thioamides, the reaction enjoys broad substrate scopes. The present catalytic system is also successfully applied to asymmetric selenation of β-substituted α,β-unsaturated thioamides. A [Cu-(R,R P )-TANIAPHOS]-SePh species is characterized by its 77 Se NMR spectra, which gives a chemical shift at δ 462 ppm. Moreover, a {[Cu-(R)-TOL-BINAP]-SePh} 2 species is characterized by X-ray analysis, which confirms the formation of CuÀ Se bond in the reaction. Finally, the transformations of the thioamide group to amine and thioester are demonstrated to be straightforward.

show abstract

Copper(I)‐Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α‐Substituted α,β‐Unsaturated Thioamides

Tian

¹

,

Zhang

²

,

Yin

³

2023

Angew Chem Int Ed

12

0

View full text Add to dashboard Cite

Herein, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and αsubstituted α,β-unsaturated thioamides is disclosed, which affords a series of chiral selenides in high to excellent enantioselectivity. As for both selenols and αsubstituted α,β-unsaturated thioamides, the reaction enjoys broad substrate scopes. The present catalytic system is also successfully applied to asymmetric selenation of β-substituted α,β-unsaturated thioamides. A [Cu-(R,R P )-TANIAPHOS]-SePh species is characterized by its 77 Se NMR spectra, which gives a chemical shift at δ 462 ppm. Moreover, a {[Cu-(R)-TOL-BINAP]-SePh} 2 species is characterized by X-ray analysis, which confirms the formation of CuÀ Se bond in the reaction. Finally, the transformations of the thioamide group to amine and thioester are demonstrated to be straightforward.

show abstract

Targeting the GSTP-dependent control of cell kinases and apoptosis with PhSeZnCl: a new seleno-organic drug

Cited by 4 publications

References 0 publications

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

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

Copper(I)‐Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α‐Substituted α,β‐Unsaturated Thioamides

Copper(I)‐Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α‐Substituted α,β‐Unsaturated Thioamides

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