Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-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(1H)-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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	6869
Journal	Molecules
Volume	28
Issue number	19
DOIs	https://doi.org/10.3390/molecules28196869
Publication status	Published - Oct 2023

Keywords

antibacterial
anticancer activity
dihydropyridin-4(1H)-ones
tetrahydropyridinylidene salts

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules28196869Licence: CC BY 4.0

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

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",

author = "Werner Seebacher and Michael Hoffelner and Ferdinand Belaj and Teresa Pirker and Muaaz Alajlani and Rudolf Bauer and Pferschy-Wenzig, {Eva Maria} and Robert Saf and Robert Weis",

note = "Publisher Copyright: {\textcopyright} 2023 by the authors.",

year = "2023",

month = oct,

doi = "10.3390/molecules28196869",

language = "English",

volume = "28",

journal = "Molecules ",

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T1 - Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-ones from 4-Amino-tetrahydropyridinylidene Salts

AU - Seebacher, Werner

AU - Hoffelner, Michael

AU - Belaj, Ferdinand

AU - Pirker, Teresa

AU - Alajlani, Muaaz

AU - Bauer, Rudolf

AU - Pferschy-Wenzig, Eva Maria

AU - Saf, Robert

AU - Weis, Robert

PY - 2023/10

Y1 - 2023/10

N2 - 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.

AB - 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.

KW - antibacterial

KW - anticancer activity

KW - dihydropyridin-4(1H)-ones

KW - tetrahydropyridinylidene salts

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U2 - 10.3390/molecules28196869

DO - 10.3390/molecules28196869

M3 - Article

AN - SCOPUS:85173799253

SN - 1420-3049

VL - 28

JO - Molecules

JF - Molecules

IS - 19

M1 - 6869

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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