Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities

Petritsch, Markus; Seebacher, Werner; Mohsin, Noor ul Amin; Dolensky, Johanna; Hochegger, Patrick; Kaiser, Marcel; Mäser, Pascal; Belaj, Ferdinand; Saf, Robert; Kretschmer, Nadine; Alajlani, Muaaz; Brantner, Adelheid; Bauer, Rudolf; Schühly, Wolfgang; Weis, Robert

doi:10.1016/j.ejmech.2020.112969

Cited by 7 publications

(3 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product is highly active for most GPB, such as S. aureus and Staphyloccus epidermidis ; however, for Gram-negative bacteria (GNB), such as E. coli and P. aeruginosa , it is less active. Most of the synthesized QASs had antimalarial activity, and the authors also found that seven products had a complete inhibitory effect on HCT1 16 (colon cancer) and U251 (glioblastoma) cancer cells . Trush et al synthesized ester-functionalized pyridine ionic liquids with different lengths of carbon chains (PyrC) and found that the antibacterial activity of the esterification products was significantly reduced compared with that of unesterified precursors.…”

Section: Chemical Diversity Of Antibacterial Qassmentioning

confidence: 99%

Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications

Zhou

Zhou²,

Zhang

et al. 2023

Bioconjugate Chem.

View full text Add to dashboard Cite

The overuse of antibiotics has led to the emergence of a large number of antibiotic-resistant genes in bacteria, and increasing evidence indicates that a fungicide with an antibacterial mechanism different from that of antibiotics is needed. Quaternary ammonium salts (QASs) are a biparental substance with good antibacterial properties that kills bacteria through simple electrostatic adsorption and insertion into cell membranes/altering of cell membrane permeability. Therefore, the probability of bacteria developing drug resistance is greatly reduced. In this review, we focus on the synthesis and application of single-chain QASs, double-chain QASs, heterocyclic QASs, and gemini QASs (GQASs). Some possible structure–function relationships of QASs are also summarized. As such, we hope this review will provide insight for researchers to explore more applications of QASs in the field of antimicrobials with the aim of developing systems for clinical applications.

show abstract

Section: Chemical Diversity Of Antibacterial Qassmentioning

confidence: 99%

Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications

Zhou

Zhou²,

Zhang

et al. 2023

Bioconjugate Chem.

View full text Add to dashboard Cite

show abstract

“…Recently, we described the synthesis and antiprotozoal potency of 4-aminotetrahydropyridinylidene salts [1] and of 1-benzyl derivatives of these salts with enhanced antiprotozoal activities [2,3]. The insertion of an additional benzyl group in ring position 3 via alkylation under basic conditions yielded 1,3-disubstituted compounds with increased antiplasmodial activity [4]. This paper reports the synthesis of 5-substituted derivatives.…”

Section: Introductionmentioning

confidence: 99%

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

Seebacher,

Hoffelner,

Belaj

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…We already described some reactions of 2,3-dihydropyridines like benzylation in ring positions 1 and 3 [15][16][17] as well as the reaction with benzoyl halides to acyl derivatives [18] and investigated the antiprotozoal, antimicrobial, and anticancer potencies of these products [15][16][17][18]. It seems that the conjugated double bond system and a nitrogen in position 4 are important for those activities, since reduction of the double bonds to a piperidine-4-amine [16] or the hydrolysis to a keto group resulted in a complete loss of activity.…”

Section: Introductionmentioning

confidence: 99%

Unexpected ring-opening of 2,3-dihydropyridines

et al. 2021

Self Cite

View full text Add to dashboard Cite

The reaction of 2,3-dihydropyridines with sulfonyl halides surprisingly yielded open chain dienes with sulfonylimine structure. The products were specific out of several possible isomers and, therefore, a separation of isomers was not necessary. All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. A bicyclic by-product from the reaction of a 2,3-dihydropyridine with mesyl chloride was isolated and its structure elucidated using a single X-ray crystal analysis. Some biological activities, like antimicrobial and cytotoxic properties were investigated. Graphic abstract

show abstract

Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities

Cited by 7 publications

References 20 publications

Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications

Quaternary Ammonium Salts: Insights into Synthesis and New Directions in Antibacterial Applications

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

Unexpected ring-opening of 2,3-dihydropyridines

Contact Info

Product

Resources

About