Evaluation of Quinazolin-2,4-Dione Derivatives as Promising Antibacterial Agents: Synthesis, In Vitro, In Silico ADMET and Molecular Docking Approaches DOI Creative Commons
Aboubakr H. Abdelmonsef, Mohamed El‐Naggar,

Amal O. A. Ibrahim

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5529 - 5529

Published: Nov. 22, 2024

A series of new quinazolin-2,4-dione derivatives incorporating amide/eight-membered nitrogen-heterocycles 2a–c, in addition, acylthiourea/amide/dithiolan-4-one and/or phenylthiazolidin-4-one 3a–d and 4a–d. The starting compound 1 was prepared by reaction 4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzoyl chloride with ammonium thiocyanate cyanoacetic acid hydrazide. strong electrophiles, namely, o-aminophenol, o-amino thiophenol, o-phenylene diamine, resulted corresponding eight-membered 2a–d. Compounds 4a–d were synthesized good-to-excellent yield through a one-pot multi-component (MCR) carbon disulfide phenyl isocyanate under mild alkaline conditions, followed ethyl chloroacetate, iodide, methyl concentrated HCl, respectively. obtained products physicochemically characterized melting points, elemental analysis, spectroscopic techniques, such as FT-IR, 1H-NMR, 13C-NMR, MS. antibacterial efficacy the eleven molecules examined vitro against two Gram-positive bacterial strains (Staphylococcus aureus Staphylococcus haemolyticus). Furthermore, Computer-Aided Drug Design (CADD) performed on derivatives, standard drug (Methotrexate), reported target enzymes (S. S. haemolyticus) to explain their binding mode actions. Notably, our findings highlight compounds 2b 2c showing both best activity docking scores targets. Finally, according ADMET predictions, possessed acceptable pharmacokinetics properties drug-likeness properties.

Language: Английский

Unveiling the Synthesis of Indole-Fused Eight-Membered Aza-Heterocycles via FeCl3–Catalyzed Radical C–N Coupling and Photophysical Studies DOI
Sakshi Singh, Maitreya Maity, Shantanu Pal

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

A novel strategy toward construction of indole-fused eight-membered heterocyclic rings through a radical pathway has been reported. Our approach involves tandem cyclization via FeCl3-catalyzed cross-dehydrogenative double C–N bond formation using DDQ as an oxidant under mild condition. An EPR experiment and time course 1H NMR study confirm that the addition triggers pyrazole N-radical, which contributes to eight-member framework with good yield. The structural diversity synthetic utility have explored, along photophysical properties synthesized compounds.

Language: Английский

Citations

0
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles DOI
Yifan Yin, Fei Liu, Miao Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 16, 2025

Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed reaction was realized by sequence EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.

Language: Английский

Citations

0
Organocatalytic Asymmetric [4 + 4] Annulation Reaction of Ynones with Unsaturated Pyrazolones: Synthesis of Eight-Membered Ether-Embedded 4,5-Fused Pyrazoles DOI
Dipankar Barman, Subhas Chandra Pan

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 20, 2025

An aminocatalytic asymmetric (4 + 4) annulation of ynones and unsaturated pyrazolones is reported. This study the first to describe an enantioselective synthesis eight-membered ether-embedded 4,5-fused pyrazoles. The scope reaction broad, cyclic ether-containing pyrazole products were isolated in moderate good yields with high enantioselectivities.

Language: Английский

Citations

0
Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles DOI

Huawei Lin,

Biming Mao, Bing Han

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2864 - 2869

Published: Jan. 1, 2024

A novel palladium-catalyzed [4 + 4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates has been developed for the synthesis bridged eight-membered oxygen heterocycles in good yields and excellent stereoselectivities.

Language: Английский

Citations

2
Highly Enantioselective Construction of Chiral Eight-Membered Cyclic Ethers through Tandem Cyclization of Ynones and Dicarbonyl Compounds DOI
Yuzhen Chen,

Peishan Gu,

Jialiang Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16736 - 16749

Published: Oct. 30, 2024

The enantioselective synthesis of eight-membered cyclic ether has always been a challenge in organic synthesis. Herein, we reported highly tandem cyclization reaction alkyne ketone and dioxypyridines mediated by chiral bifunctional catalysts. This generates two adjacent stereocenters using an atomeconomic manner, providing simple effective method for the one-step ethers.

Language: Английский

Citations

2
Editorial: Heterodienes in organic synthesis DOI Creative Commons
Alexey Yu. Sukhorukov

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: April 8, 2024

EDITORIAL article Front. Chem., 08 April 2024Sec. Organic Chemistry Volume 12 - 2024 | https://doi.org/10.3389/fchem.2024.1403024

Language: Английский

Citations

0
Evaluation of Quinazolin-2,4-Dione Derivatives as Promising Antibacterial Agents: Synthesis, In Vitro, In Silico ADMET and Molecular Docking Approaches DOI Creative Commons
Aboubakr H. Abdelmonsef, Mohamed El‐Naggar,

Amal O. A. Ibrahim

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5529 - 5529

Published: Nov. 22, 2024

A series of new quinazolin-2,4-dione derivatives incorporating amide/eight-membered nitrogen-heterocycles 2a–c, in addition, acylthiourea/amide/dithiolan-4-one and/or phenylthiazolidin-4-one 3a–d and 4a–d. The starting compound 1 was prepared by reaction 4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzoyl chloride with ammonium thiocyanate cyanoacetic acid hydrazide. strong electrophiles, namely, o-aminophenol, o-amino thiophenol, o-phenylene diamine, resulted corresponding eight-membered 2a–d. Compounds 4a–d were synthesized good-to-excellent yield through a one-pot multi-component (MCR) carbon disulfide phenyl isocyanate under mild alkaline conditions, followed ethyl chloroacetate, iodide, methyl concentrated HCl, respectively. obtained products physicochemically characterized melting points, elemental analysis, spectroscopic techniques, such as FT-IR, 1H-NMR, 13C-NMR, MS. antibacterial efficacy the eleven molecules examined vitro against two Gram-positive bacterial strains (Staphylococcus aureus Staphylococcus haemolyticus). Furthermore, Computer-Aided Drug Design (CADD) performed on derivatives, standard drug (Methotrexate), reported target enzymes (S. S. haemolyticus) to explain their binding mode actions. Notably, our findings highlight compounds 2b 2c showing both best activity docking scores targets. Finally, according ADMET predictions, possessed acceptable pharmacokinetics properties drug-likeness properties.

Language: Английский

Citations

0