Small ring heterocycles, such as epoxides and aziridines, are present in several natural products and are also highly versatile building blocks, frequently involved in the synthesis of numerous bioactive products and pharmaceuticals. Because of the potential for increased efficiency and selectivity, along with the advantages of environmentally benign synthetic procedures, multicomponent reactions (MCRs) have been explored in the synthesis and ring opening of these heterocyclic units. In this review, the recent advances in MCRs involving the synthesis and applications of epoxides and aziridines to the preparation of other heterocycles are discussed emphasizing the stereoselectivity of the reactions.
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http://dx.doi.org/10.3390/molecules24030630 | DOI Listing |
Se Pu
January 2025
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
Lipids are indispensable components of living organisms and play pivotal roles in cell-membrane fluidity, energy provision, and neurotransmitter transmission and transport. Lipids can act as potential biomarkers of diseases given their abilities to indicate cell-growth status. For example, the lipid-metabolism processes of cancer cells are distinct from those of normal cells owing to their rapid proliferation and adaptation to ever-changing biological environments.
View Article and Find Full Text PDFBioorg Med Chem
December 2024
School of Science, Monash University (Malaysia Campus), Jalan Lagoon Selatan, Bandar Sunway, 47500 Selangor, Malaysia. Electronic address:
Scaffold-based drug design has become increasingly prominent in the pharmaceutical field due to the systematic and effective approach through which it facilitates the development of novel drugs. The identification of key scaffolds provides medicinal chemists with a fundamental framework for subsequent research. With mounting evidence suggesting that increased aromaticity could impede the chances of developmental success for oral drug candidates, there is an imperative need for a more thorough exploration of alternative ring systems to mitigate attrition risks.
View Article and Find Full Text PDFChemistry
December 2024
Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.
Cyclophellitol is a potent and selective mechanism-based retaining β-glucosidase inhibitor that has served as a versatile starting point for the development of activity-based glycosidase probes (ABPs). We developed routes of synthesis of eight mono- and dideoxycyclophellitols and cyclophellitol aziridines, the latter as ABPs carrying either a biotin or fluorophore linked to the aziridine nitrogen. We reveal the potency of these 24 compounds as inhibitors of the three human retaining β-glucosidases, GBA1, GBA2 and GBA3.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Department of Chemistry, University of Liverpool, Crown Street, Liverpool, United Kingdom, L69 7ZD.
Chem Sci
August 2024
Department of Chemistry, University of Bayreuth Bayreuth 95447 Germany
Three-membered rings, such as epoxides, aziridines, oxaziridines, cyclopropenes, vinyloxaziridines, and azirines, are recognized as crucial pharmacophores and building blocks in organic chemistry and drug discovery. Despite the significant advances in the synthesis of these rings through photo/electrochemical methods over the past decade, there has currently been no focused discussion and updated overviews on this topic. Therefore, we presented this review article on the efficient synthesis of three-membered rings using photo- and electrochemical strategies, covering the literature since 2015.
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