Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies

Abstract

Six novel quaternary ammonium derivatives of 4-pyrrolidino pyridine were prepared and isolated via a facile one-pot synthesis and a simple purification procedure. The purity and the molecular structure of the 4-pyrrolidino pyridine derivatives were confirmed with 1H and 13C NMR spectroscopy and powder X-ray diffraction techniques. The crystal structures of the compounds were characterized by single crystal X-ray diffraction (SCXRD) and their thermal properties were studied by Differential Scanning Calorimetry (DSC) analyses. The antibacterial properties of the title compounds against five bacterial strains were evaluated using Kirby–Bauer disk diffusion susceptibility test. The compounds crystallize in the monoclinic or orthorhombic crystal systems (space groups: P21/c, P21/n, or P212121) and their crystal structures are stabilized by a combination of intra- and intermolecular halogen bonding interactions, short contacts and π-π interactions. Above interactions, they contribute to the thermal stability and lack of phase transition effects up to 350 °C. Two of the compounds possess antibacterial effect against E. coli or S. aureus bacterial strains—similar or better than the kanamycin reference.

Synthesis, Structural and Behavioral Studies of Indole Derivatives D2AAK5, D2AAK6 and D2AAK7 as Serotonin 5-HT1A and 5-HT2A Receptor Ligands

“…Next, D2AAK5 was subjected to X-ray studies. Interatomic distances and bond angles of D2AAK5 are in the expected ranges [ 26 ] and are comparable to those observed in the related indole [ 7 , 17 , 18 , 19 , 27 , 28 ] and 3,4-dihydro-2 H -1,5-benzodioxepine [ 29 , 30 , 31 ] derivatives.…”

Quaternary Ammonium Compounds (QACs) and Ionic Liquids (ILs) as Biocides: From Simple Antiseptics to Tunable Antimicrobials

“…Rusew and colleagues presented a work, in which long lipophilic tails in QACs were replaced by more compact aryl-containing substituents (Figure 14) [63].…”

“…Rusew and colleagues presented a work, in which long lipophilic tails in QACs were replaced by more compact aryl-containing substituents (Figure 14) [63]. Bogdanov and colleagues explored the microbiological effect of isatin-based QACs (Figure 13) [62].…”

“…Rusew and colleagues presented a work, in which long lipophilic tails in QACs were replaced by more compact aryl-containing substituents (Figure 14) [63]. The results of a broad antibacterial screening appeared to be nontypical for cationic biocides.…”

Natural and Modified Zeolite Clinoptilolite with Antimicrobial Properties: a Review

“…Nowadays, the issue of the continuing growth of microbial resistance to antibiotics and antimicrobial agents (Davies et al, 2013) and the elevation of microbial-related diseases necessitate the needs of improvement of antimicrobial agents or the development of new products that can replace the existing non-effective commercial antimicrobial agents (So et al, 2010). In recent decades, a wide range of different antimicrobial agents has been used successfully, such as antibiotics (Zilberman and Elsner, 2008;Campoccia et al, 2013) antimicrobial peptides (Kazemzadeh-Narbat et al, 2013;Glinel et al, 2012), individual elements (Lemire et al, 2013;Cloutier et al, 2015), enzymes (Eby et al, 2009;Zhou et al, 2014;Milenkovic et al, 2015), organic cations compounds (del Olmo et al, 2020;Rusew et al, 2020;Xin et al, 2020), organic non-cationic compounds (Baveja et al, 2004;Kazemzadeh-Narbat et al, 2013) and other inorganic compounds (Rtimi et al, 2013;Michl et al, 2015;Storm et al, 2015). Many antimicrobial materials cannot support disinfection properties in the long term per se.…”