New Quinoline Derivatives as Potential Multitherapeutic Agents: A Facile Synthesis via an Epoxide Ring Opening Reaction, Characterization, DFT Calculations, and Molecular Docking DOI

Rahima Khelaf,

Amani Direm,

Farida Hakkar

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(14)

Опубликована: Апрель 1, 2025

Abstract A mixture of three newly synthesized quinoline derivatives, namely 1‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)ethane‐1,2‐diol ( 6 ), 2‐bromo‐2‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)ethan‐1‐ol 7 and 1‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)‐2‐hydroxyethyl nitrate 8 ) were prepared by treating 2,6‐dimethoxy‐3‐oxiranylquinoline 5 with cerium(IV) ammonium (CAN) in the presence N ‐bromosuccinimide (NBS). The compounds fully characterized FT‐IR, 1 H, 13 C‐NMR, HRMS. Their molecular structures optimized DFT/B3LYP/6–311++G( d , p discussed comparison experimental closely‐related molecules, 2,6‐dimethoxyquinoline‐3‐carbonitrile (DQC). results obtained are good agreement X‐ray data geometry DQ. effect substituents’ groups on ring – was thoroughly analyzed. evaluation frontier orbitals showed that HOMOs localized ring, oxygen bromine atoms, whereas all LUMOs situated ring. Furthermore, a natural population analysis (NPA) conducted therefore atomic charges discussed. computed global reactivity descriptors presented promising biological properties hence their endorsement docking simulations against Staphylococcus aureus topoisomerase II gyrase A, Escherichia coli DNA B, Candida albicans dihydrofolate reductase, human I, cyclooxygenase‐2 (COX2). H‐bonds, hydrophobic contacts, π∙∙∙π stacking, which resulted potential antimicrobial, antitumor, anti‐inflammatory efficiency .

Язык: Английский

New Quinoline Derivatives as Potential Multitherapeutic Agents: A Facile Synthesis via an Epoxide Ring Opening Reaction, Characterization, DFT Calculations, and Molecular Docking DOI

Rahima Khelaf,

Amani Direm,

Farida Hakkar

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(14)

Опубликована: Апрель 1, 2025

Abstract A mixture of three newly synthesized quinoline derivatives, namely 1‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)ethane‐1,2‐diol ( 6 ), 2‐bromo‐2‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)ethan‐1‐ol 7 and 1‐(5‐bromo‐2,6‐dimethoxyquinolin‐3‐yl)‐2‐hydroxyethyl nitrate 8 ) were prepared by treating 2,6‐dimethoxy‐3‐oxiranylquinoline 5 with cerium(IV) ammonium (CAN) in the presence N ‐bromosuccinimide (NBS). The compounds fully characterized FT‐IR, 1 H, 13 C‐NMR, HRMS. Their molecular structures optimized DFT/B3LYP/6–311++G( d , p discussed comparison experimental closely‐related molecules, 2,6‐dimethoxyquinoline‐3‐carbonitrile (DQC). results obtained are good agreement X‐ray data geometry DQ. effect substituents’ groups on ring – was thoroughly analyzed. evaluation frontier orbitals showed that HOMOs localized ring, oxygen bromine atoms, whereas all LUMOs situated ring. Furthermore, a natural population analysis (NPA) conducted therefore atomic charges discussed. computed global reactivity descriptors presented promising biological properties hence their endorsement docking simulations against Staphylococcus aureus topoisomerase II gyrase A, Escherichia coli DNA B, Candida albicans dihydrofolate reductase, human I, cyclooxygenase‐2 (COX2). H‐bonds, hydrophobic contacts, π∙∙∙π stacking, which resulted potential antimicrobial, antitumor, anti‐inflammatory efficiency .

Язык: Английский

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