Direct diazo-transfer reaction on β-lactam: Synthesis and preliminary biological activities of 6-triazolylpenicillanic acids

Bioorganic & Medicinal Chemistry
2007.0

Abstract

In this study we report the first example of a direct diazo-transfer reaction on readily available 6-aminopenicillanates to give 6-azidopenicillanates in high yield. Subsequent Cu(I)-catalyzed Huisgen cycloaddition between these 6-azidopenicillanates and assorted terminal alkynes facilely furnished 6-triazolylpenicillanic acids. Preliminary biological screening indicates that these triazolylpenicillanic acids possess low to moderate antibacterial activities.

Knowledge Graph

Similar Paper

Direct diazo-transfer reaction on β-lactam: Synthesis and preliminary biological activities of 6-triazolylpenicillanic acids
Bioorganic & Medicinal Chemistry 2007.0
Synthesis and antimicrobial activity of β-lactam–bile acid conjugates linked via triazole
Bioorganic & Medicinal Chemistry Letters 2008.0
Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-[(1,2,3-triazol-1-yl)methyl]-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide and related triazolyl derivatives
Journal of Medicinal Chemistry 1987.0
Allyl and propargyl substituted penam sulfones as versatile intermediates toward the syntheses of new β-lactamase inhibitors
Bioorganic & Medicinal Chemistry Letters 2001.0
Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity
Bioorganic & Medicinal Chemistry Letters 2008.0
Application of Huisgen (3+2) cycloaddition reaction: Synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations
European Journal of Medicinal Chemistry 2010.0
1H-1,2,3-Triazolyl-substituted 1,3,4-oxadiazole derivatives containing structural features of ibuprofen/naproxen: Their synthesis and antibacterial evaluation
Bioorganic & Medicinal Chemistry Letters 2016.0
Ultrasound-assisted synthesis of novel 1,2,3-triazoles coupled diaryl sulfone moieties by the CuAAC reaction, and biological evaluation of them as antioxidant and antimicrobial agents
European Journal of Medicinal Chemistry 2014.0
Diazo Transfer−Click Reaction Route to New, Lipophilic Teicoplanin and Ristocetin Aglycon Derivatives with High Antibacterial and Anti-influenza Virus Activity: An Aggregation and Receptor Binding Study
Journal of Medicinal Chemistry 2009.0
The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels–Alder adducts
Bioorganic & Medicinal Chemistry Letters 2006.0