scholarly journals Design, Synthesis and Tumour-Selective Toxicity of Novel 1-[3-{3,5-Bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone Oximes and Related Quaternary Ammonium Salts

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7132
Author(s):  
Praveen K. Roayapalley ◽  
Jonathan R. Dimmock ◽  
Lisett Contreras ◽  
Karol S. Balderrama ◽  
Renato J. Aguilera ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Selectivity Index ◽  
Ammonium Salts ◽  
Colon Cancer Cells ◽  
Selective Toxicity ◽  
Design Synthesis ◽  
Structure Activity ◽  
In Series ◽  
Quantitative Structure Activity Relationships

A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a–h and related quaternary ammonium salts 4a–h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells revealed the compounds in series 3 and 4 to be potent cytotoxins with submicromolar CC50 values in virtually all cases. In contrast, the compounds were less cytocidal towards HGF, HPLF and HPC non-malignant cells revealing their tumour-selective toxicity. Quantitative structure–activity relationships revealed that, in general, both cytotoxic potency and selectivity index figures increased as the magnitude of the Hammett sigma values rose. In addition, 3a–h are cytotoxic towards a number of leukemic and colon cancer cells. 4b,c lowered the mitochondrial membrane potential in CEM cells, and 4d induced transient G2/M accumulation in Ca9-22 cells. Five compounds, namely 3c,d and 4c–e, were identified as lead molecules that have drug-like properties.

Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Anna Brol
Keyword(s):  
Phosphonic Acid ◽  
Quaternary Ammonium ◽  
Alkylating Agent ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Aminoalkylphosphonic Acid

An effective protocol for quaternization of simple 1-aminoalkylphosphonic acids under basic conditions and using Me2SO4 as convenient alkylating agent is reported. In the course of reaction phosphonic acid quaternary ammonium...

scholarly journals Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2424 ◽  
Author(s):  
Tăbăcaru ◽  
Botezatu ◽  
Horincar ◽  
Furdui ◽  
Dinică
Keyword(s):  
Escherichia Coli ◽  
Triticum Aestivum ◽  
Seed Germination ◽  
Quaternary Ammonium ◽  
Pathogenic Bacteria ◽  
Classical Method ◽  
Triticum Aestivum L ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Radicle Growth

A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 hours were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination.

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