AI Article Synopsis
- Lactams are important compounds used in treating various diseases like cancer and diabetes, and are found in many pharmaceuticals.
- The addition of fluorine groups, particularly trifluoromethyl, can significantly change the properties of these organic molecules.
- The review discusses key biological targets and synthesis methods for different lactam types while identifying promising lactam structures for future drug development.
Article Abstract
Lactams are a crucial class of compounds with broad therapeutic applications, including in the treatment of cancer, diabetes, and infectious diseases. Functionalised lactams are essential core structures in numerous alkaloids and pharmaceuticals. The introduction of fluorine-containing groups, such as a trifluoromethyl (CF) group, into organic molecules significantly alters their physical and chemical properties. This review highlights the primary biological targets, as well as the most important synthetic pathways, associated with trifluoromethylated β-lactams (four-atom rings), γ-lactams (five-atom rings), δ-lactams (six-atom rings), and ε-lactams (seven atom rings). Furthermore, we analyze the most common lactam scaffolds, evaluating their potential for future chemical synthesis and emphasizing those that merit attention despite having limited reported analogues. This article aims to provide a comprehensive overview of the importance of trifluoromethylated lactams in drug discovery and design.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d4cc05324a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Trifluoromethylated lactams: promising small molecules in the search for effective drugs.
Chem Commun (Camb)
December 2024
Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
Article Synopsis
- Lactams are important compounds used in treating various diseases like cancer and diabetes, and are found in many pharmaceuticals.
- The addition of fluorine groups, particularly trifluoromethyl, can significantly change the properties of these organic molecules.
- The review discusses key biological targets and synthesis methods for different lactam types while identifying promising lactam structures for future drug development.
Fixing the Achilles Heel of Pfizer's Paxlovid for COVID-19 Treatment.
J Med Chem
July 2024
Chemistry Research Laboratory, Department of Chemistry and the Ineos Oxford Institute for Antimicrobial Research, University of Oxford, 12 Mansfield Road, OX1 3TA Oxford, United Kingdom.
Nirmatrelvir (PF-07321332), a first-in-class inhibitor of the severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) main protease (M), was developed by Pfizer under intense pressure during the pandemic to treat COVID-19. A weakness of nirmatrelvir is its limited metabolic stability, which led to the development of a combination therapy (paxlovid), involving coadministration of nirmatrelvir with the cytochrome P450 inhibitor ritonavir. However, limitations in tolerability of the ritonavir component reduce the scope of paxlovid.
View Article and Find Full Text PDFTrifluoromethylnitrone: a versatile building block for synthesizing trifluoromethyl-containing heterocyclic compounds.
Org Biomol Chem
July 2024
Department of Chemistry, Aligarh Muslim University, Aligarh-202002, India.
This review explores the significance of trifluoromethylnitrones in synthesizing fluorine-containing compounds, with a particular focus on trifluoromethylated heterocycles. It explores the versatility of trifluoromethylnitrones, especially in [3 + 2] cycloaddition reactions, highlighting their unique reactivity with various dienophile substrates. Trifluoromethylnitrones are valuable precursors for the rapid synthesis of medicinally important trifluoromethylated heterocycles, including isoxazolidines, dihydroisoxazoles, oxathiazolidines, β-lactams, and aziridines.
View Article and Find Full Text PDFFluorinated captopril analogues inhibit metallo-β-lactamases and facilitate structure determination of NDM-1 binding pose.
Eur J Med Chem
February 2024
Department of Chemistry, UiT The Arctic University of Norway, NO-9037, Tromsø, Norway. Electronic address:
Bacterial resistance to the majority of clinically used β-lactam antibiotics is a global health threat and, consequently, the driving force for the development of metallo-β-lactamase (MBL) inhibitors. The rapid evolution of new MBLs calls for new strategies and tools for inhibitor development. In this study, we designed and developed a series of trifluoromethylated captopril analogues as probes for structural studies of enzyme-inhibitor binding.
View Article and Find Full Text PDFSynthesis, Reactivity, and Antibacterial Activity of -Difluoroalkene, Difluoromethyl, and Trifluoromethyl β-Lactams.
Org Lett
January 2024
BioCIS UMR 8076 CNRS, Building Henri Moissan, Université Paris-Saclay, 17 avenue des sciences, 91400 Orsay, France.
New -difluoroalkenes were synthesized by the dehydrofluorination of the corresponding 4-CF-β-lactams. An unexpected rearrangement mechanism of the ester moiety dependent on a stabilizing negative charge was observed. Hydrogenation to 4-CHF-β-lactams was successful from -difluoro-β-lactams.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!