Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c5pp00009b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Positively-charged, chalcone-hydroxypyrone hybrid ruthenium(II)-arene complexes functionalized with ethacrynic acid: Synthesis, characterizaion, and antitumor effect.
J Inorg Biochem
February 2025
Key Laboratory of Chemical Biology of Hebei Province; Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education; State Key Laboratory of New Pharmaceutical Preparations and Excipients, College of Chemistry & Materials Science, Hebei University, Baoding 071002, China. Electronic address:
A new family of ethacrynic acid-functionalized, chalcone-hydroxypyrone hybrid ruthenium(II)-arene complexes (4a-4e) have been designed, synthesis and fully characterized by H and C NMR, ESI-MS, elemental analysis, and melting point tests. The molecular structure of 3a, one of the precursor complexes, has been determined by single-crystal X-ray diffraction. The cytotoxicity of the obtained complexes toward human cancer cell lines such as HeLa, MGC803, A549, MDA-MB-231, and MCF-7 cells have been investigated by MTT assay.
View Article and Find Full Text PDFUtilizing MEDT analysis of [3 + 2] cycloaddition reaction: x-ray crystallography of spirooxindole linked with thiophene/furan heterocycles and triazole framework.
BMC Chem
November 2024
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia.
Hybridization of spirooxindole with different pharmacophores such as triazole and heterocycle such as thiophene and furan moiety was achieved by the [3 + 2] cycloaddition (32CA) reaction approach. Structural investigations of the compounds 4a and 4b were performed using X-ray single crystal structure determinations and Hirshfeld analysis. Both compounds crystallized in monoclinic crystal system.
View Article and Find Full Text PDFDesign and Synthesis of Pyridyl and 2-Hydroxyphenyl Chalcones with Antitubercular Activity.
Molecules
September 2024
Leicester School of Pharmacy, De Montfort University, Leicester LE1 9BH, UK.
A focussed library of pyridyl and 2-hydroxyphenyl chalcones were synthesized and tested for growth inhibitory activity against H37Rv, and normal and cancer breast cell lines. Pyridyl chalcones bearing lipophilic A-ring, e.g.
View Article and Find Full Text PDF-chalcones obtained one-pot synthesis as the anti-neurodegenerative agents and their effect on the HT-22 cell line.
Heliyon
September 2024
Department of Biotechnology and Cell Biology, Medical College, University of Information Technology and Management in Rzeszow, Sucharskiego 2, 35-225, Rzeszów, Poland.
In the area of research on neurodegenerative diseases, the current challenge is to search for appropriate research methods that would detect these diseases at the earliest possible stage, but also new active structures that would reduce the rate of the disease progression and minimize the intensity of their symptoms experienced by the patient. The chalcones are considered in the context of candidates for new drugs dedicated to the fight against neurodegenerative diseases. The synthesis of -chalcone derivatives as aim molecules was performed.
View Article and Find Full Text PDFOne-Pot Multienzyme Cascades for Stereodivergent Synthesis of Tetrahydroquinolines.
Angew Chem Int Ed Engl
December 2024
Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Sanjay Gandhi Postgraduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow, 226014, INDIA.
The tetrahydroquinoline (THQ) framework is commonly found in natural products and pharmaceutically relevant molecules. Apart from using transition metal catalysts and chiral phosphoric acids, the chiral 2-substituted 1,2,3,4-THQs are synthesized using amine oxidase biocatalysts. However, the use of imine reductases (IREDs) in their asymmetric synthesis remained unexplored.
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!