Multicomponent reactions have long been recognized as some of the most versatile tools in organic chemistry, with extensive applications in biomedical science and the pharmaceutical industry. In this study, we explored the potential of the Passerini reaction by designing and synthesizing new low molecular mass gelators that can serve as novel formulations for prolonged anesthesia. These gelators address critical issues like poor solubility, low bioavailability, and short plasma half-life, all of which hinder therapeutic efficacy. To further understand the gelation mechanism, we performed density functional theory (DFT) calculation for confirming the presence of non-covalent interactions during gel formation. Additionally, we evaluated the antimicrobial properties of the synthesized compounds, aiming to counter the rise of infectious diseases. These innovative antimicrobial agents could offer solutions to the growing problem of antibiotic resistance, which renders many existing therapies ineffective. Overall, this study aims to develop advanced formulations and antimicrobial agents through the Passerini reaction, providing new strategies for treating infections, minimizing side effects, and combating antibiotic resistance.
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http://dx.doi.org/10.1002/cmdc.202400774 | DOI Listing |
ChemMedChem
January 2025
Central University of Haryana, Chemistry, Academic Block-1, Jant-Pali, 123 031, Mahendergarh, INDIA.
Multicomponent reactions have long been recognized as some of the most versatile tools in organic chemistry, with extensive applications in biomedical science and the pharmaceutical industry. In this study, we explored the potential of the Passerini reaction by designing and synthesizing new low molecular mass gelators that can serve as novel formulations for prolonged anesthesia. These gelators address critical issues like poor solubility, low bioavailability, and short plasma half-life, all of which hinder therapeutic efficacy.
View Article and Find Full Text PDFCarbohydr Polym
March 2025
Université Claude Bernard Lyon 1, INSA Lyon, Université Jean Monnet, CNRS UMR 5223, Ingénierie des Matériaux Polymères, F-69621 Cédex, France. Electronic address:
Passerini reaction was advantageously exploited to hydrophobize carboxymethyl cellulose (CMC) and alginates (ALG) by employing various hydrophobic aldehydes and isocyanides. The Passerini reaction, carried out in ecofriendly conditions, allowed to design never described twofold hydrophobized polysaccharide derivatives via the covalent grafting of two hydrophobic moieties. The modified CMC and ALG products were in-depth characterized to guaranty the success of the modification and to calculate the degrees of substitution (DS).
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, Seoul National University, Seoul 08826, Korea.
Sequence-defined polymers composed of a large pool of chemically distinct monomers (SDPs) have been pursued to achieve the structural and functional precisions exhibited by biopolymers in nonbiological environments. In contrast to the incremental growth of SDPs by sequential addition of individual monomers, the iterative exponential growth (IEG) method allows the synthesis of high molecular-weight SDPs, but their sequences have been composed mostly of binary monomers. Consequently, achieving high molecular-weight SDPs built with a large pool of monomers remains a challenge.
View Article and Find Full Text PDFMolecules
November 2024
LAQV-REQUIMTE, Institute for Research and Advanced Studies, University of Évora, Rua Romão Ramalho, 59, 7000-641 Évora, Portugal.
The 3-component Passerini reaction (3CPR), discovered little more than 100 years ago, has been demonstrated in the last few decades to be a valuable tool for accessing structural diversity and complexity, essential topics to consider in drug discovery programs. Focusing on accessing a fine-tuned family of α-acyloxyamide-oxindole hybrids, we underline herein our latest insights regarding the use of this mild reaction approach to obtain promising anticancer agents. Cheap and commercially available isatin was used as starting material.
View Article and Find Full Text PDFFront Chem
September 2024
Advanced Materials Division, Mintek, Randburg, South Africa.
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