A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K CO (10 mol%) with high efficiency in water/ethanol as green solvent at room temperature. This protocol proceeded via Claisen-Schmidt condensation and Michael addition. The present methodology offers several advantages, such as short reaction time, high yield, more readily available and inexpensive materials, more environmentally friendly, no need for column chromatography, simple work-up procedure, and the absence of volatile and hazardous organic solvents.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chir.22653 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Licochalcone A-Inspired Chalcones: Synthesis and Their Antiproliferative Potential in Prostate Cancer Cells.
Molecules
December 2024
Department of Chemistry & Biochemistry, California State University, Fresno, CA 93740, USA.
Prostate cancer remains a significant global health concern, prompting ongoing exploration of novel therapeutic agents. Licochalcone A, a natural product in the chalcone family isolated from licorice root, is characterized by its enone structure and demonstrates antiproliferative activity in the micromolar range across various cell lines, including prostate cancer. Building on our prior success in enhancing curcumin's antiproliferative potency by replacing the substituted phenol with a 1-alkyl-1H-imizadol-2-yl moiety, we applied a similar approach to design a new class of licochalcone A-inspired chalcones.
View Article and Find Full Text PDFBioprospecting hydroxylated chalcones in model of ischemia-reoxygenation and probing NOX4 interactions via molecular docking.
Biol Chem
December 2024
Postgraduate Program in Pharmacology, 28121 Federal University of Ceara, Fortaleza, CE, Brazil.
Ischemia/reperfusion injury (I/R) is a leading cause of acute kidney injury (AKI) in conditions like kidney transplants, cardiac surgeries, and nephrectomy, contributing to high global mortality and morbidity. This study aimed to analyze the protective effects of 2'-hydroxychalcones in treating I/R-induced AKI by targeting key pathological pathways. Considering strong antioxidant action along with other pharmacological roles of chalcone derivatives, six 2'-hydroxychalcones were synthesized via Claisen-Schmidt condensation and analyzed for their protective effects in an I/R induced AKI model using HK-2 cells.
View Article and Find Full Text PDFDesign, Synthesis and Pro-Inflammatory Activity of Palmitoylated Derivatives of Thioglycolic Acid as New Immunomodulators.
Chem Biol Drug Des
December 2024
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, Assiut, Egypt.
The immune system is essential for the defense against infections and is critically implicated in various disorders, including immunodeficiency, autoimmunity, inflammation and cancer. The current study includes a new design of palmitoylated derivatives of thioglycolic acids (PTGAs) capable of triggering innate immune responses. The new series were accessible through a three-step synthetic route, including N-palmitoylation, Claisen-Schmidt condensation and thia-Michael addition.
View Article and Find Full Text PDFBrominated chalcones as promising antileishmanial agents.
Bioorg Med Chem Lett
February 2025
Departamento de Química, Universidade Federal de Sergipe, Aracaju, Brazil.
Leishmaniasis is a group of diseases caused by protozoa of the genus Leishmania. They are considered neglected diseases and are endemic to tropical and subtropical regions, affecting thousands of people annually. Leishmaniasis has a wide global distribution, present on four continents.
View Article and Find Full Text PDFSynthesis of -Chalcones Based on Green Chemistry Strategies and Their Cytotoxicity Toward Human MeWo and A375 Melanoma Cell Lines.
Molecules
October 2024
Department of Medical Biology, Wroclaw Medical University, Chalubinskiego 3, 50-368 Wrocław, Poland.
Chalcone is an aromatic ketone that forms the central core of many important biological compounds. Chalcone derivatives show various biological activities, especially anti-inflammatory, antibacterial, antioxidant, and anticancer activities, and also inhibit melanoma cell growth. In this study, we synthesized chalcone compounds with -chalcone's chemical structure under microwave (MW) and microwave-ultrasound (MW-US) conditions and compared them to chalcones produced using the classical synthesis method.
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!