Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1 H)-ones from 4-Amino-tetrahydropyridinylidene Salts

Werner Seebacher; Michael Hoffelner; Ferdinand Belaj; Teresa Pirker; Muaaz Alajlani; Rudolf Bauer; Eva-Maria Pferschy-Wenzig; Robert Saf; Robert Weis

doi:10.3390/molecules28196869

Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1 H)-ones from 4-Amino-tetrahydropyridinylidene Salts

Molecules. 2023 Sep 29;28(19):6869. doi: 10.3390/molecules28196869.

Authors

Werner Seebacher¹, Michael Hoffelner¹, Ferdinand Belaj², Teresa Pirker³, Muaaz Alajlani⁴, Rudolf Bauer³, Eva-Maria Pferschy-Wenzig³, Robert Saf⁵, Robert Weis¹

Affiliations

¹ Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, University of Graz, Schubertstrasse 1, 8010 Graz, Austria.
² Institute of Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria.
³ Pharmacognosy, Institute for Pharmaceutical Sciences, University of Graz, Beethovenstrasse 8, 8010 Graz, Austria.
⁴ Faculty of Pharmacy, Al-Sham Private University, 011 Damascus, Syria.
⁵ Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria.

Abstract

Various 4-aminotetrahydropyridinylidene salts were treated with aldehydes in an alkaline medium. Their conversion to 5-substituted β-hydroxyketones in a one-step reaction succeeded only with an aliphatic aldehyde. Instead, aromatic aldehydes gave 5-substituted β-aminoketones or a single δ-diketone. The new compounds were characterized using spectroscopic methods and a single crystal structure analysis. Some of them showed anticancer and antibacterial properties.

Keywords: antibacterial; anticancer activity; dihydropyridin-4(1H)-ones; tetrahydropyridinylidene salts.

Grants and funding

Open access funding by the University of Graz.