One-Step Synthesis of 2-Arylquinolin-4(1H)-Ones from 1-(2-Aminoaryl)-3-Arylpropan-1-Ones via Pd(II)-Catalyzed Dehydrogenative Cyclization DOI

Hyuck-Jae Won,

Seung Hwan Son,

Yo‐Sep Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 90(1), P. 98 - 108

Published: Dec. 31, 2024

In this study, we developed palladium-catalyzed dehydrogenative cyclization to transform 1-(2-aminoaryl)-3-arylpropan-1-ones into 2-arylquinolin-4(1H)-ones, also known as aza-flavones which are the bioisosteres of flavones, in an atom-economic manner. This method exhibited excellent chemical compatibility with a broad substrate scope, accommodating up 25 derivatives. Additionally, kinetic studies were performed elucidate reaction mechanism. Further, 2-phenylquinolin-4(1H)-one was used common intermediate for synthesizing privileged structures such 4-methoxyquinoline, N-methylquinoline-4(1H)-one, and 4-(pseudo)halogenated quinoline moieties.

Language: Английский

Targeting cancer using scaffold-hopping approaches: illuminating SAR to improve drug design DOI

Shivani,

Towhidur Rahaman, Sandeep Chaudhary

et al.

Drug Discovery Today, Journal Year: 2024, Volume and Issue: 29(9), P. 104115 - 104115

Published: July 26, 2024

Language: Английский

Citations

3
Unlocking the power of imidazoquinolines: recent advances in anticancer and immunotherapeutic strategies DOI

Ranjini Jenifer R,

Badruzzaman Choudhury,

Mohammed Mujahid Alam

et al.

Future Medicinal Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 17

Published: April 15, 2025

The challenges in drug discovery aiming to mitigate cancer progression are the thrust area of scientific research for several decades. Since advent heterocyclic chemistry, programs have made significant achievements that lead development numerous drugs with broad spectrum potencies, contributing both diagnostic and therapeutic advancements. Till date, efforts discover more potent efficient candidates underway minimize adverse side effects existing chemotherapeutics. In view above, small-molecule agonists can interact different immune modulators like toll receptor-7 (TLR-7) TLR-8 being investigated explored. These expected display profound effect on anti-tumoral activity by enhancing production proinflammatory cytokines. Recently, imidazoquinoline derivatives proven TLR agonist activities emerged as promising anticancer therapeutics. With advancements technology evolution new scopes discovery, strategies adopted, particularly help nanotechnology, immune-technology, combination etc., curb various types cancers. Herein, novel therapeutics imidazoquinolines reported last 5 years, their structure-activity relationship along important synthetic schemes agonists, discussed.

Language: Английский

Citations

0
Vistas in the domain of 3-acetyl-4-hydroxy-2-quinolinone derivatives (AHQ) and their applications DOI Creative Commons

Nedaa N. Elnaggar,

Wafaa S. Hamama, Eslam A. Ghaith

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(23), P. 18034 - 18088

Published: Jan. 1, 2025

This review discusses the significant advances in current status and latest synthesis techniques for N -substituted 3-acetyl-4-hydroxyquinolinones.

Language: Английский

Citations

0
Special Issue: “Rational Design and Synthesis of Bioactive Molecules” DOI Open Access
Irena Kostova

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(18), P. 9927 - 9927

Published: Sept. 14, 2024

The rational design of novel bioactive molecules is a critical but challenging task in drug discovery [...]

Language: Английский

Citations

1
Synthesis of Thiaphenanthridinones from Sulfinate Esters and 2-Borylanilines DOI Creative Commons
Keisuke Nakamura,

Minori Suzuki,

Suguru Yoshida

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9676 - 9681

Published: Nov. 6, 2024

A facile palladium-catalyzed synthesis of thiaphenanthridinones from sulfinate esters and 2-borylanilines is disclosed. Various sulfur analogs phenanthridinones were synthesized by bromide-selective cross-coupling cyclization in one step. Further transformations the obtained allowed preparing a broad range thiaphenanthridinone derivatives involving bioactive compounds.

Language: Английский

Citations

1
Synthesis of azaflavanones and alpha-ylidene azaflavanones DOI
Erick M.C. Pinheiro,

Rafael P. R. F. de Oliveira,

Sandro J. Greco

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 167, P. 134295 - 134295

Published: Oct. 10, 2024

Language: Английский

Citations

0
One-Step Synthesis of 2-Arylquinolin-4(1H)-Ones from 1-(2-Aminoaryl)-3-Arylpropan-1-Ones via Pd(II)-Catalyzed Dehydrogenative Cyclization DOI

Hyuck-Jae Won,

Seung Hwan Son,

Yo‐Sep Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 90(1), P. 98 - 108

Published: Dec. 31, 2024

In this study, we developed palladium-catalyzed dehydrogenative cyclization to transform 1-(2-aminoaryl)-3-arylpropan-1-ones into 2-arylquinolin-4(1H)-ones, also known as aza-flavones which are the bioisosteres of flavones, in an atom-economic manner. This method exhibited excellent chemical compatibility with a broad substrate scope, accommodating up 25 derivatives. Additionally, kinetic studies were performed elucidate reaction mechanism. Further, 2-phenylquinolin-4(1H)-one was used common intermediate for synthesizing privileged structures such 4-methoxyquinoline, N-methylquinoline-4(1H)-one, and 4-(pseudo)halogenated quinoline moieties.

Language: Английский

Citations

0