Back to Search
Start Over
Efficient and stereoselective synthesis of sugar fused pyrano[3,2- c ]pyranones as anticancer agents.
- Source :
-
RSC advances [RSC Adv] 2023 Aug 18; Vol. 13 (35), pp. 24604-24616. Date of Electronic Publication: 2023 Aug 18 (Print Publication: 2023). - Publication Year :
- 2023
-
Abstract
- A highly stereoselective, efficient and facile route was achieved for the synthesis of novel and biochemically potent sugar fused pyrano[3,2- c ]pyranone derivatives starting from inexpensive, naturally occurring d-galactose and d-glucose. First, β- C -glycopyranosyl aldehydes were synthesized from these d-hexose sugars in six steps, with overall yields 41-55%. Next, two different 1- C -formyl glycals were synthesized from these β- C -glycopyranosyl aldehydes by treatment in basic conditions. The optimization of reaction conditions was carried out following reactions between 1- C -formyl galactal and 4-hydroxycoumarin. Next, 1- C -formyl galactal and 1- C -formyl glucal were treated with nine substituted 4-hydroxy coumarins at room temperature (25 °C) in ethyl acetate for ∼1-2 h in the presence of l-proline to obtain exclusively single diastereomers of pyrano[3,2- c ]pyranone derivatives in excellent yields. Four compounds were found to be active for the MCF-7 cancer cell line. The MTT assay, apoptosis assay and migration analysis showed significant death of the cancer cells induced by the synthesized compounds.<br />Competing Interests: The authors declare no competing financial interest.<br /> (This journal is © The Royal Society of Chemistry.)
Details
- Language :
- English
- ISSN :
- 2046-2069
- Volume :
- 13
- Issue :
- 35
- Database :
- MEDLINE
- Journal :
- RSC advances
- Publication Type :
- Academic Journal
- Accession number :
- 37601594
- Full Text :
- https://doi.org/10.1039/d3ra02371k