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Flavanones [2-aryl-2,3-dihydrochromen-4(1)ones] and 2-aryl-2,3-dihydroquinolin-4(1)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and catalysis that make it useful in an undergraduate organic chemistry laboratory. The use of both microwave irradiation as a source of energy to promote reactions and efficient catalysts are considered within green chemistry principles, mostly because the reaction yields are improved and reaction time decreased. In this paper, the efficiency of microwave irradiation use in the synthesis of chalcone derivatives and efficient catalyst systems to promote their isomerization into flavanones and 2-aryl-2,3-dihydroquinolin-4(1)-ones is demonstrated.
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http://dx.doi.org/10.3390/mps2030070 | DOI Listing |
Nat Commun
May 2025
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing, 100191, China.
Hydroxysafflor yellow A (HSYA) is a clinical investigational new drug for the treatment of acute ischemic stroke. It has a unique quinochalcone di-C-glycoside structure and is exclusively found in the flowers of safflower (Carthamus tinctorius). To date, little is known about the biosynthesis of HSYA.
View Article and Find Full Text PDFJ Org Chem
May 2025
College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators as Innovative Medicine, Chongqing University of Arts and Sciences, Chongqing 402160, China.
A solvent-controlled strategy to regulate the site-selectivity of free phenols and stereospecificity of 1,4-addition is presented, thereby divergently producing 4'-hydroxyflavanone and 2'-hydroxyflavanone site-specific C-H bond functionalization. This protocol is applicable to a diverse range of free phenols. Furthermore, this strategy efficiently accesses natural product-like frameworks, including Eriodictyol, Narigenin, (+)-Anastatins A, (+)-Anastatins B, and (+)-Cycloaltilisin 7 with high selectivity.
View Article and Find Full Text PDFFood Chem
May 2025
School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou, 510006, China. Electronic address:
Naringenin is a plant flavonoid found in citrus fruits and is known for its anti-inflammatory and antioxidant activities. However, extracting high-purity naringenin from citrus fruits and separating its enantiomers remains challenging. This study synthesized a molecularly imprinted multiple-component covalent organic framework (MI COF) with abundant imprinted recognition sites for the first time.
View Article and Find Full Text PDFAntioxidants (Basel)
December 2024
Dipartimento di Chimica e Tecnologie Chimiche, Università Della Calabria, Via Pietro Bucci Cubo 12/D, I-87030 Rende, CS, Italy.
A novel and efficient analytical protocol based on paper spray tandem mass spectrometry was developed for the determination of isomeric -glycoside flavanones in citrus juices and beverages. This approach significantly reduces sample preparation time and solvent consumption compared to traditional chromatographic techniques. By exploiting the unique fragmentation patterns of these compounds, accurate quantification of both diglycosides and their individual isomers (neohesperidoside and rutinose derivatives) was achieved.
View Article and Find Full Text PDFBiomed Chromatogr
November 2024
Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia.
Thirteen flavanone racemates were successfully separated using a Chiralpak® IA column and isopropanol-hexane (50:50, v/v). The mobile phase flow rate and detection wavelength were 0.5 mL/min and 254 nm.
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