Selenocompounds as Potent Efflux Pump Inhibitors on Gram‐positive Bacteria DOI Creative Commons
Annamária Kincses, Nikoletta Szemerédi,

Miguel Benito‐Lama

et al.

ChemMedChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

Abstract In recent years, selenocompounds have gained increasing attention as potential anticancer and antibacterial agents. Several selenoderivatives been confirmed to act MDR efflux pump inhibitors, based on their in vitro results against the bacterial AcrAB‐TolC system cancer P‐glycoprotein. Efflux pumps can contribute directly or indirectly virulence of bacteria, they reduce intracellular concentration substances by expelling them out cell. The present work aims study inhibiting properties four families selenoesters, namely aspirin‐selenoesters, phenone‐selenoesters, hydroxy‐selenoesters, benzyl‐selenoesters. real‐time ethidium bromide accumulation assay that these derivatives inhibited systems methicillin‐resistant Staphylococcus aureus (MRSA) without exerting any effect. relative expression gene NorA transporter was also monitored presence most potent reference S. , finding could change tested gene. Regarding anti‐biofilm activity, benzyl‐selenoesters, hydroxy‐selenoesters efficiently inhibit biofilm production MRSA strain. It be concluded thus reducing biofilm‐producing bacteria.

Language: Английский

Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes DOI

Keming Yang,

Tian Feng, Youai Qiu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(45)

Published: Sept. 12, 2023

Despite widespread use of the deuterium isotope effect, selective labeling chemical molecules remains a major challenge. Herein, facile and general electrochemically driven, organic mediator enabled deuteration styrenes with oxide (D2 O) as economical source was reported. Importantly, this transformation could be suitable for various electron rich mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition-metal catalysts, affording desired products in good yields excellent D-incorporation (D-inc, up to >99 %). Mechanistic investigations means experiments cyclic voltammetry tests provided sufficient support transformation. Notably, method proved powerful tool late-stage biorelevant compounds.

Language: Английский

Citations

48
Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade DOI

Shaogao Zeng,

Yong Zeng, Hui Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4074 - 4084

Published: Feb. 23, 2024

Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis 3-selenylazaflavanones 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, provided selenylated products in moderate to excellent yields high regio- stereoselectivity. could also be readily scaled up efficiency. Detailed mechanistic studies through control experiments disclosed that selenium-based radical might participate this transformation.

Language: Английский

Citations

10
A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis DOI Creative Commons
Nian Li, Ruzal Sitdikov, Ajit Prabhakar Kale

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2500 - 2566

Published: Oct. 9, 2024

With the resurgence of electrosynthesis in organic chemistry, there is a significant increase number routes available for late-stage functionalization (LSF) drugs. Electrosynthetic methods, which obviate need hazardous chemical oxidants or reductants, offer unprecedented control reactions through continuous variation applied potential and possibility combination with photochemical processes. This capability substantial advantage performing electrochemical photoelectrochemical LSF. Ultimately, these protocols are poised to become vital component medicinal chemist's toolkit. In this review, we discuss that have been demonstrated be applicable LSF pharmaceutical drugs, their derivatives, natural substrates. We present analyze representative examples illustrate electrochemistry photoelectrochemistry valuable molecular scaffolds.

Language: Английский

Citations

6
Solvent‐Regulated Electrochemical Selenylation and Deuteration of Alkynyl Aryl Ketones: Chemoselective Synthesis of 3‐Selenylated Chromones and Deutero‐Selenylated Chalcones DOI Open Access

Balati Hasimujiang,

Juyu Zhu,

Wenyan Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(17), P. 2929 - 2935

Published: July 21, 2023

Abstract We have developed an electrochemical reaction for the synthesis of 3‐selenylchromones and deutero‐selenylated chalcones alkynyl aryl ketones. This method is free from metal catalysts oxidants, regulated by solvents. The conditions are mild, a wide range substrates can be employed to produce selenylated chromones chalcones, displaying potential anti‐inflammatory activities. Furthermore, we demonstrated applicability this approach late‐stage deutero‐selenylation drug molecule, metochalcone.

Language: Английский

Citations

16
Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review DOI Creative Commons
Zhixiong Ruan,

Balati Hasimujiang

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 511 - 520

Published: Oct. 1, 2023

Abstract Electrochemical synthesis, due to its environmentally benign, sustainable, and practical nature, has become an appealing powerful substitute for traditional methods oxidizing reducing organic compounds. Thus, numerous valuable changes have been established in the field of synthesis through utilization electrochemistry. Among these electrochemical transformations, formation C–Se bonds stands out as exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary progress utilizing strategies synthesizing organoselenium

Language: Английский

Citations

12
Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes DOI
Xiang Liu, Yuan Zhang, Yi Zheng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1367 - 1372

Published: Feb. 23, 2024

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions. electrochemical C—H proceeded smoothly to afford ( E )‐vinyl sulfones good selectivity in an undivided cell without external oxidant. While aerobic trifunctionalization occurred presence KI air, which provides β ‐keto selenosulfones via formation C—O, C—S, and C—Se bonds one‐pot. Following control experiments, a plausible mechanism is proposed rationalize experimental results.

Language: Английский

Citations

4
Modular Synthesis of Bioactive Selenoheterocycles for Efficient Cancer Therapy via Electrochemical Selenylation/Cyclization DOI
Wenyan Xu,

Chengwei Zheng,

Mu Chen

et al.

Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

A green, efficient, and environmentally friendly electrochemical strategy was developed for synthesizing a series of selenoheterocyclic compounds. The antitumor activities these compounds were evaluated, revealing that 4o, 5n, 5o demonstrated remarkable efficacy. These effectively inhibited lung cancer by inducing cell apoptosis, causing DNA damage, suppressing the progression epithelial-mesenchymal transition. Notably, compound identified as first inhibitor DEAD-box helicase 10 (DDX10). An in vivo xenograft assay further confirmed therapeutic potential 5o, demonstrating tumor growth inhibition rates 60%, 78%, 88% at doses 5 mg/kg, 20 respectively. This study highlights promising chemotherapeutic agent effective treatment cancer.

Language: Английский

Citations

0
Direct Electrooxidative Selenylamination of Alkynes: Access to 3‐Selenylindoles DOI Open Access

Balati Hasimujiang,

Yong Zeng,

Shifeng Zou

et al.

Israel Journal of Chemistry, Journal Year: 2023, Volume and Issue: 64(1-2)

Published: July 24, 2023

Abstract A novel metal‐ and oxidant‐free electrooxidative selenylamination of o ‐aminophenacetylenes with diselenides for achieving 3‐selenylindoles has been developed moderate to excellent yield. The reaction proceeded smoothly a broad substrate scope highly functional group tolerance. synthetic practicality this innovative approach was demonstrated by its easy scalability. Moreover, mechanistic studies revealed that an in‐situ generated selenium cation might be the key intermediate electrochemical selenocyclization process.

Language: Английский

Citations

10
Synthesis of β‐Hydroxyselenides via Electrochemical Hydroxyselenenylation of Alkenes with Diselenides and H2O DOI
Weiwei Li, Yingyuan Hu,

Junsheng Hou

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(5)

Published: Feb. 2, 2024

Abstract A practical electrochemical method for the synthesis of β‐hydroxyselenides has been developed under an external oxidant‐free condition at room temperature air from alkenes with diselenides and H 2 O. radical mechanism is proposed this transformation gram‐scale reactions demonstrate practicability reaction.

Language: Английский

Citations

3
Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions DOI
Hang‐Dong Zuo,

Huafeng Yan,

Yuting Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

Citations

0