Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 16, Issue -, Pages 2862-2869Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.16.235
Keywords
antiproliferative activity; 1,2-dihydropyridines; green Hantzsch synthesis; heterogeneous catalysis; one-pot multicomponent reaction
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Funding
- European Union-European Social Fund (ESF) under the Operational Programme II-Cohesion Policy 2014-2020, Investing in human capital to create more opportunities and promote the well-being of society
- Spanish Government (MCIU/AEI/FEDER, UE) [PGC2018-094503-B-C22]
- EU Social Fund (FSE) [TESIS2020010055]
- Canary Islands ACIISI [TESIS2020010055]
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A rapid route for obtaining unsymmetrical 1,2-dihydropyridines (1,2-DHPs) as opposed to 1,4-dihydropyridines (1,4-DHPs) has been achieved via a one-pot multicomponent Hantzsch reaction. A benign protocol has been developed for the preparation of various 1,2-dihydropyridine derivatives using heterogenized phosphotungstic acid on alumina support (40 wt %). High yields of over 75% have been accomplished in just 2-3.5 h after screening several heterogeneous catalysts and investigating the optimal reaction conditions. The catalyst chosen has passed the heterogeneity test and was shown to have the potential of being reused for up to 8 consecutive cycles before having a significant loss in activity. In addition, aromatic aldehydes gave the aforementioned regioisomer while the classical 1,4-DHPs were obtained when carrying out the reaction using aliphatic aldehydes. The preliminary study of the antiproliferative activity against human solid tumor cells demonstrated that 1,2-DHPs could inhibit cancer cell growth in the low micromolar range.
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