Iron-Borophosphate Glass-Catalyzed Regioselective Hydrothiolation of Alkynes under Green Conditions DOI Open Access

Nicoli Catholico,

Eduarda A. Tessari,

Isis Juliane Arantes Granja

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(7), P. 1127 - 1127

Published: July 20, 2023

Vinyl sulfides are an important class of organic compounds that have relevant synthetic and biological applications. The best-known approach to realize these is the hydrothiolation alkynes under different conditions using metals, toxic carcinogenic solvents. development new catalysts materials environmentally friendly, low in cost, easy handle highly desirable for this reaction. In regard, glasses become materials, since they can be used as a catalyst chemical reactions. We prepared characterized inexpensive robust iron-doped borophosphate glass (Fe@NaH2PO4-H3BO3 glass). This eco-friendly material was successfully applied solvent-free conditions, affording desired vinyl good-to-excellent yields, with high stereoselectivity. method synthesis attractive because it enables reuse iron-glass scaling up

Language: Английский

Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions DOI

Kaili Cen,

Yuan Liu,

Junhong Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8632 - 8640

Published: June 6, 2024

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, preliminary experiments revealed that reaction probably proceeded cation instead radical pathway.

Language: Английский

Citations

6
Selenylated Imidazo [1,2-a]pyridine Induces Apoptosis and Oxidative Stress in 2D and 3D Models of Colon Cancer Cells DOI Creative Commons
Giovana Bicudo Gomes,

Claudia Stutz Zubieta,

Jhefferson dos Santos Guilhermi

et al.

Pharmaceuticals, Journal Year: 2023, Volume and Issue: 16(6), P. 814 - 814

Published: May 30, 2023

Colon cancer incidence rates are increasing annually, a scenario aggravated by genetic and epigenetic alterations that promote drug resistance. Recent studies showed novel synthetic selenium compounds more efficient less toxic than conventional drugs, demonstrating biocompatibility pro-oxidant effects on tumor cells. This study aimed to investigate the cytotoxic effect of MRK-107, an imidazo [1,2- a]pyridine derivative, in 2D 3D cell culture models colon (Caco-2 HT-29). Sulforhodamine B results revealed GI50 2.4 µM for Caco-2, 1.1 HT-29, 22.19 NIH/3T3 cultures after 48 h treatment. Cell recovery, migration, clonogenic, Ki-67 corroborated MRK-107 inhibits proliferation prevents regeneration metastatic transition selectively reducing migratory clonogenic capacity; non-tumor cells (NIH/3T3) re-established 18 h. The oxidative stress markers DCFH-DA TBARS increased ROS generation damage. Caspases-3/7 activated induce apoptosis as main mode death both models, assessed annexin V-FITC acridine orange/ethidium bromide staining. is selective, redox-active compound with pro-apoptotic properties capacity activate antiproliferative pathways, showing promise anticancer research.

Language: Английский

Citations

10
Selenium-Containing (Hetero)Aryl Hybrids as Potential Antileishmanial Drug Candidates: In Vitro Screening against L. amazonensis DOI Creative Commons
Maria Helena Fermiano,

Amarith R. das Neves,

Fernanda da Silva

et al.

Biomedicines, Journal Year: 2024, Volume and Issue: 12(1), P. 213 - 213

Published: Jan. 17, 2024

Leishmaniasis remains a significant global health concern, with current treatments relying on outdated drugs associated high toxicity, lengthy administration, elevated costs, and drug resistance. Consequently, the urgent need for safer more effective therapeutic options in leishmaniasis treatment persists. Previous research has highlighted selenium compounds as promising candidates innovative therapy. In light of this, library 10 selenium-containing diverse was designed evaluated this study. These included selenium-substituted indole, coumarin, chromone, oxadiazole, imidazo[1,2-a]pyridine, Imidazo[2,1-b]thiazole, oxazole, among others. were screened against Leishmania amazonensis promastigotes intracellular amastigotes, their cytotoxicity assessed peritoneal macrophages, NIH/3T3, J774A.1 cells. Among tested compounds, MRK-106 MRK-108 displayed highest potency L. reduced cytotoxicity. Notably, exhibited IC50 values 3.97 µM 4.23 µM, respectively, most showed low host cells (CC50 > 200 µM). Also, MRK-107 MRK-113 activity amastigotes (IC50 18.31 15.93 SI 12.55 10.92, respectively). conclusion, identified hold potential structures antileishmanial to be further explored subsequent studies. findings represent step toward development therapies leishmaniasis, addressing pressing novel improved treatments.

Language: Английский

Citations

3
An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones DOI
Liu‐Liang Mao, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110784 - 110784

Published: Dec. 1, 2024

Language: Английский

Citations

3
Selectfluor-mediated tandem cyclization of enaminones with diselenides toward the synthesis of 3-selenylated chromones DOI Creative Commons

Ji-Hong Xia,

Qian Chen, Jinwei Yuan

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(38), P. 26948 - 26959

Published: Jan. 1, 2023

A practical and metal-free approach for the regioselective selenation of chromones employing Selectfluor reagent under mild conditions is described. The developed method suitable a wide substrate scope affords 3-selenylated in good to excellent yield with high selectivity. An ionic mechanism proposed this transformation. Furthermore, application potassium thiocyanate enaminones synthesis thiocyano transformation also successful.

Language: Английский

Citations

6
Trihaloisocyanuric Acids: Useful Reagents for Halogenation Reactions and Heterocyclic Scaffold Construction DOI
Marcio C. S. de Mattos

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(14), P. 1079 - 1101

Published: May 6, 2024

Abstract: Trihaloisocyanuric acids [1,3,5-trihalo-1,3,5-triazine-2,4,6-(1H,3H,5H)-triones] are commercially available or easily prepared solids. They highly reactive, stable, handled, and have an excellent atom economy, transferring up to three halogen atoms organic substrates. In these regards, the present review summarizes their synthetic applications as safe convenient reagents. Therefore, electrophilic halogenation reactions of alkenes, alkynes, arenes, heteroarenes, carbonyl compounds, heteroatoms, well radical involving saturated substrates in situ halogenated intermediates for Appel-type presented discussed. Remarkably, trihaloisocyanuric processes construction heteroarene scaffolds based on halo- oxidative cyclization, multicomponent reactions, telescopic also given.

Language: Английский

Citations

2
KIO3-catalyzed selective oxidation of thiols to disulfides in water under ambient conditions DOI

José R. L. Sousa,

Marcelo S. Franco, Leila Dorácio Mendes

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(11), P. 2175 - 2181

Published: Dec. 19, 2023

Herein, we report a KIO

Language: Английский

Citations

4
3‐Halochromones Through Oxidative α‐Halogenation of Enaminones and its Photophysical Investigation: Another Case of Photo‐induced Partially Aromatised Intramolecular Charge Transfer? DOI
José S. S. Neto,

Filipe T. Coelho,

Carlos V. Doerner

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 19(2)

Published: Dec. 16, 2023

Abstract A versatile synthesis strategy for fluorescent 3‐halo‐4 H ‐chromen‐4‐one derivatives is reported. The method involves the oxidative α‐halogenation of enaminones performed by an efficient and sustainable oxidation system. use Oxone ® in combination with KCl, KBr, or KI enables preparation 3‐chloro‐, 3‐bromo‐, 3‐iodo‐4 good to excellent yields, great functional group tolerance where protocol amenable gram‐scale synthesis. analysis photophysical properties presented 4 showed absorption UV region fluorescence emission violet‐to‐cyan a relatively large Stokes shift. In solution, all compounds present dual emission, regardless solvent, assigned partially aromatised intramolecular charge transfer mechanism, considering presence pseudo‐aromatic ring chromone scaffold absence influence substituent electronic features optical behaviour.

Language: Английский

Citations

3
Ag(i)-catalyzed three-component radical cascade synthesis of 3-organoselenyl chromones from 2-methoxyaryl alkynones, Se powder and organic boronic acids DOI
Nan Sun,

Zengguo Qiao,

Xiaolong Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(47), P. 21670 - 21676

Published: Jan. 1, 2023

A new three-component radical cascade process has been proposed for the synthesis of 3-organoselenyl chromones from 2-methoxyaryl alkynones, Se powder and organic boronic acids.

Language: Английский

Citations

2
Selenium-Containing (Hetero)Aryl Hybrids as Potential Antileishmanial Drug Candidates: In vitro Screening Against L. amazonensis DOI Open Access
Maria Helena Fermiano,

Amarith R. das Neves,

Fernanda Trombetta

et al.

Published: Dec. 21, 2023

Leishmaniasis remains a significant global health concern, with current treatments relying on outdated drugs associated high toxicity, lengthy administration, elevated costs, and drug resistance. Consequently, the urgent need for safer more effective therapeutic options in leishmaniasis treatment persists. Previous research has highlighted selenium compounds as promising candidates innovative therapy. In light of this, library 10 selenium-containing diverse was designed evaluated this study. The were subjected to screening against L. amazonensis promastigotes, their cytotoxicity assessed NIH/3T3 cells. Among tested compounds, MRK-106 MRK-108 displayed highest potency promastigotes while demonstrating reduced cytotoxicity. Notably, exhibited IC50 values 3.97 µM, 4.23 respectively, most showed low cells (CC50 > 200 µM). Although these results are promising, additional investigations focusing intracellular amastigotes required determine antileishmanial activity compounds. conclusion, identified hold considerable potential warrant further exploration subsequent studies. These findings represent step towards development therapies leishmaniasis, addressing pressing novel improved treatments.

Language: Английский

Citations

1