Recent advances in the syntheses and reactions of biologically promising β-lactam derivatives

Tetrahedron, Journal Year: 2025, Volume and Issue: 177, P. 134565 - 134565

Published: Feb. 28, 2025

Language: Английский

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Rapid Access to Chiral Spiro[2.3] Lactams: Stereoselective Hydroborylation and Hydrosilylation and Remote Control of Axial Chirality by Copper-Catalyzed Desymmetrization of Spirocyclopropenes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1941 - 1946

Published: Feb. 28, 2024

Chiral spirocyclopropyl β-lactams are common motifs in bioactive compounds and pharmaceuticals. Here we disclose a diastereoselective enantioselective hydroborylation hydrosilylation of spirocyclopropenes, via Cu-catalyzed desymmetrization strategy, for the rapid preparation enantio-enriched β-lactams. The efficient strategy allows remote control axial chirality, offering borylated silylated products bearing central, spiro, chirality. combination multichiral elements would provide novel motif biological evaluation potential drug discovery.

Language: Английский

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Diverse Annulations of Alkyl(phenyl)phosphinic Chlorides and Imines

Organic Letters, Journal Year: 2025, Volume and Issue: 27(6), P. 1417 - 1421

Published: Jan. 30, 2025

The reactivity of alkyl(aryl)phosphinic chlorides and imines was investigated in the presence a base. results indicated that allyl/benzyl(aryl)phosphinic gave rise to 1,2-azaphosphines (δ-phostims), while nonbenzylic produced corresponding β-phosphinolactams (β-phostims) their reaction with cyclic dibenzo[b,f][1,4]oxazepines, whereas steric electron-rich arylmethyl(aryl)phosphinic generated [2 + 2 2] annuloadducts some cases. current investigation provides useful insight into phosphinic imines.

Language: Английский

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Chiral β‐Lactams by Ruthenium‐Catalyzed Enantioselective CH Carbene Insertion

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

Published: April 16, 2025

A ruthenium‐catalyzed intramolecular carbenoid insertion into a C(sp 3 )  H bond leads to the enantioselective formation of chiral β‐lactams. The reaction is catalyzed by ruthenium complex featuring pyridine‐2,6‐bis(oxazoline) ligand, combined with cyclometalated phenylimidazo[1,5‐ ]pyridine ligand. This belongs recently introduced new class catalysts ( Angew. Chem. Int. Ed. 2020 , 59 12393). Starting from N ‐benzyl α‐diazoacetamides, β‐lactams are provided in up 82% isolated yield 98% enantiomeric excess, without any occurrence Buchner side reaction. Mechanistic experiments reveal that β‐lactam (4‐membered ring) inherently favored over more common γ‐lactam (5‐membered formation.

Language: Английский

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Synthesis of lactones and lactams via C(sp³)–H bond functionalization

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this review, we have showcased the diverse aspects of transition-metal catalysis, biocatalysis, and photocatalytic C(sp 3 )–H bond functionalization to access lactones lactams.

Language: Английский

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An insights into structural diversity of β-lactam scaffold towards varied medicinal applications: A comprehensive update (2020–2024)

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 153, P. 155383 - 155383

Published: Nov. 16, 2024

Language: Английский

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Chemical Methods for the Construction of Spirocyclic β-Lactams and Their Biological Importance

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: July 18, 2024

Abstract Spirocyclic β-lactams are a family of natural and synthetic chemicals with different biological activities, including antibacterial properties, interact critical physiological targets such as T-type calcium channels acetyl-CoA cholesterol acyltransferase. Their unique chemical structure, combining spiro ring system β-lactam group, offers promising opportunities for the targeted discovery medications in medicinal chemistry. have potential to be adaptable frameworks developing novel therapeutic medicines particular three-dimensional pharmacophoric characteristics increased efficacy. Numerous methods employed synthesis spirocyclic β-lactams, cyclization, functional group modifications, asymmetric utilizing chiral catalysts biomimetic approaches. In this short review, two distinct approaches describing recent syntheses (from 2021 2024) discussed. The first is based on constructing ring, while other entails transforming monocyclic into structures. These include detailed reaction processes descriptions functions target spirocycles. applications chemistry highlight their role structurally diverse compounds significant potential, demonstrating creative building complex molecular 1 Introduction 2 β-Lactam Ring Synthesis 3 Non-β-Lactam 4 Miscellaneous Examples 5 Conclusion Outlook

Language: Английский

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Design, synthesis, characterization, antimicrobial evaluations and molecular docking studies of 5-(phenylcarbamoyl)pentylselenyl tethered ester, acid and trans -β-lactams

Journal of Sulfur Chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 20

Published: Dec. 10, 2024

Herein, we unveil the utility of bis(5-phenylcarbamoylpentyl)diselenide 2 for obtaining unique seleno-ester viz ethyl 2-(5-(phenylcarbamoyl)pentylselenyl)ethanoate 3 and further transformation to 2-(5-(phenylcarbamoyl)pentylselenyl)ethanoic acid 4. Next, time-efficient (complete in 15 min.) stereoselective synthesis trans-3-((5-phenylcarbamoyl)pentylselenyl)-β-lactams 6a-d (52-78% yields) starting from seleno-acid 4 substituted imines 5a-d has been reported with relevant characterization data (FT-IR, FT-NMR (1H, 13C), CHN elemental analysis). In vitro antibacterial antifungal biological evaluation silico molecular docking studies exhibit a profound dependence on nature functionality (functionalized selenyl- /ester / β-lactam) anchored 5-(phenylcarbamoyl)pentylselenyl chain. antimicrobial evidenced trans-seleno-β-lactam 6c (incorporating p-methoxyphenyl substituents both at N1 C4 atoms β-lactam ring) be active against all tested gram positive bacterial (S. aureus, B. subtilis), negative (E. coli, P. aeruginosa) fungal (C. albicans) species exhibiting 9-20 mm 8-12 diameter inhibition zones. trans-β-Lactam 6b (with C4-phenyl N1-p-methylphenyl groups) exhibited maximum zone (14 S. aureus) amongst trans-6a-d. Molecular results ligand binding affinity are observed well agreement making these seleno-compounds potential candidates medicinal importance.

Language: Английский

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Emerging Trends in Microwave and Ultrasound/Visible Light/ Carbene Intermediates & Carbonylation/Metal-Catalyzed Mediated Synthesis of β-Lactams (2021-2024)

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134429 - 134429

Published: Dec. 1, 2024

Language: Английский

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Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications

Chemical Science, Journal Year: 2024, Volume and Issue: 15(36), P. 14668 - 14676

Published: Jan. 1, 2024

A novel and highly diastereoselective NBS-mediated cyclization of N -alkoxy α,β-unsaturated silyl imino ethers to furnish nearly three dozen α-bromo β-lactams with dual functional handles is described.

Language: Английский

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