Recent Advances in Pyridine Scaffold: Focus on Chemistry, Synthesis, and Antibacterial Activities

BioMed Research International, Год журнала: 2023, Номер 2023(1)

Опубликована: Янв. 1, 2023

Multidrug-resistant (MDR) pathogens have created a fatal problem for human health and antimicrobial treatment. Among the currently available antibiotics, many are inactive against MDR pathogens. In this context, heterocyclic compounds/drugs play vital role. Thus, it is very much essential to explore new research combat issue. Of nitrogen-bearing compounds/drugs, pyridine derivatives of special interest due their solubility. Encouragingly, some newly synthesized found inhibit multidrug-resistant S. aureus (MRSA). Pyridine scaffold bearing poor basicity generally improves water solubility in pharmaceutically potential molecules has led discovery numerous broad-spectrum therapeutic agents. Keeping these mind, we reviewed chemistry, recent synthetic techniques, bacterial preventative activity since 2015. This will facilitate development pyridine-based novel antibiotic/drug design near future as versatile with limited side effects next-generation therapeutics.

Язык: Английский

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Zn(II)-Catalyzed Multicomponent Sustainable Synthesis of Pyridines in Air

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3650 - 3665

Опубликована: Фев. 28, 2023

Herein, we report a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines using alcohols as the primary feedstock NH4OAc nitrogen source. Using well-defined air-stable Zn(II)-catalyst, 1a, featuring redox-active tridentate azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (La), wide variety unsymmetrical 2,4,6-substituted were prepared by three-component coupling secondary with NH4OAc. Catalyst 1a is equally compatible four-component coupling. Unsymmetrical also via alcohol two different A series up to 67% yield 1-phenylpropan-1-one or 1,2-diphenylethan-1-one The 1a-catalyzed reactions proceeded efficiently upon replacing corresponding ketones, producing desired in higher yields shorter reaction time. few control experiments performed unveil mechanistic aspects, which indicates that active participation aryl-azo ligand during catalysis enables Zn(II)-complex act an efficient catalyst for present multicomponent reactions. Aerial oxygen acts oxidant dehydrogenation alcohols, H2O H2O2 byproducts.

Язык: Английский

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Recent developments in the synthesis of azaindoles from pyridine and pyrrole building blocks

Organic Chemistry Frontiers, Год журнала: 2020, Номер 8(3), С. 466 - 513

Опубликована: Ноя. 26, 2020

The azaindole framework is ubiquitous in bioactive natural products and pharmaceuticals. This review highlights the synthetic approaches to azaindoles with advantages limitations, mechanistic pathways biological importance.

Язык: Английский

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A concise review on some synthetic routes and applications of pyridine scaffold compounds

Current Chemistry Letters, Год журнала: 2021, Номер 10(4), С. 337 - 362

Опубликована: Янв. 1, 2021

Different methods for the synthesis of pyridine derivatives as well chemical reactivity profiles and structures these substances are reviewed. The utility compounds precursors is emphasized in many heterocycles that pharmacologically active organic agrochemicals. This review results from a literature survey containing some synthetic applications derivatives.

Язык: Английский

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Selective Synthesis of Substituted Pyridines and Pyrimidines through Cascade Annulation of Isopropene Derivatives

Organic Letters, Год журнала: 2022, Номер 24(8), С. 1620 - 1625

Опубликована: Фев. 23, 2022

Diverse substituted pyridines and pyrimidines with high selectivity were obtained using a concise efficient protocol developed herein. The reaction proceeds via metal-free cascade annulation of isopropene derivatives. Using derivatives as C3 synthons, NH4I the "N" source, formaldehyde or dimethyl sulfoxide carbon this realizes formation intermolecular C-N C-C bonds.

Язык: Английский

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NH₄OAc-Promoted Domino Route to Hydroxyarylated Unsymmetrical Pyridines under Neat Conditions

The Journal of Organic Chemistry, Год журнала: 2019, Номер 85(4), С. 2151 - 2167

Опубликована: Дек. 25, 2019

A new metal-, oxidant-, and solvent-free ecofriendly domino method has been established for modular synthesis of a diverse range medicinally promising hydroxyarylated unsymmetrical pyridines in good to high chemical yields with an excellent regioselectivity. This process involves N-sulfonyl ketimines as C,N-binucleophiles, enolizable ketones, aromatic/heteroaromatic aldehydes using ammonium acetate ideal promoter under neat conditions, which creates two C-C bonds one C-N bond. Notably, the neutral reaction conditions are mild enough tolerate functionalities cover variety substrates, thus bestowing powerful avenue access tri- tetrasubstituted including carbo- heterocyclic fused ones. Interestingly, practical, scalable, high-yielding pyridylphenol derivatives was successfully accomplished by our unique method.

Язык: Английский

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Primary amine C–N bond cleavage for the synthesis of multi-substituted pyridine and pyrrole derivatives

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(3), С. 780 - 785

Опубликована: Дек. 9, 2022

Synthesis of multi-substituted pyridines and pyrroles was established involved C-N bond cleavage new C–N C–C formation. The adjacent to the primary carbon 1,2-diamino-2-methylpropane selectively cleaved.

Язык: Английский

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Sources, Transformations, Syntheses, and Bioactivities of Monoterpene Pyridine Alkaloids and Cyclopenta[c]pyridine Derivatives

Molecules, Год журнала: 2022, Номер 27(21), С. 7187 - 7187

Опубликована: Окт. 24, 2022

Monoterpene pyridine alkaloids (MTPAs) are derived from iridoid glycosides (IGs). The common molecular structure of MTPAs is the ring, while some them have a cyclopenta[c]pyridine skeleton. Some compounds containing this potentially bioactive medicinal agents. In paper, seven drug candidates (A-G), ninety natural source products (1-90), thirty-seven synthesized (91-127), as well twenty-six key intermediates (S1-S26) were summarized. We categorized five types and one type in all. Additionally, their possible genetic pathways proposed. Then, chemical transformation, biotransformation, synthesis, bioactivity derivatives analyzed Cyclopenta[c]pyridine can be concisely chirally synthesized, they shown potentials with antibacterial, insecticidal, antiviral, anti-inflammatory, neuropharmacological activities.

Язык: Английский

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Sustainable Four-Component Annulation for the Synthesis of 2,3,4,6-Tetraarylpyridines

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(5), С. 3897 - 3906

Опубликована: Фев. 17, 2021

A one-pot, four-component annulation of 2,3,4,6-tetraarylpyridines from aromatic aldehydes, methyl ketones, diaryl ethanones, and ammonium acetate is described. The reaction features high functional group compatibility in air under solvent-free conditions without any additive only water as the nontoxic byproduct, providing a strategy for facile, economical, eco-friendly construction multiaryl-substituted pyridines simple readily available reactants.

Язык: Английский

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A Metal-Free Visible-Light Photoredox Construction and Direct C–H Functionalization of Pyridines: Green Synthesis of Polysubstituted Picolinaldehydes

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 17244 - 17248

Опубликована: Ноя. 22, 2021

The development of a novel environmental benign and sustainable synthetic method for highly efficient construction direct C-H functionalization N-heterocycles remains pivotal central research topic organic medicinal chemistry. Herein, visible-light-enabled biomimetic aza-6π electrocyclization assembly diverse pyridines further tandem Minisci-type reaction were developed. A broad spectrum polysubstituted picolinaldehydes readily constructed with high efficacy good functional group tolerance under metal- oxidant-free conditions.

Язык: Английский

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