Biological Activity of Quinolinium Salts

Gutsulyak, B. M.

doi:10.1070/rc1972v041n02abeh002038

Cited by 14 publications

(9 citation statements)

References 3 publications

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“…Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010). The antibacterial significance of synthetic quinolinium derivatives has been discovered by many scientists (Babalola, 1998;Collier et al, 1953;Gutsulyak, 1972). Due to these well-known bioactivities of quinolinium chemophores, our research group has designed and synthesized several quinolinium stilbene derivatives in order to investigate their ability to overcome some of Gram-positive and Gram-negative pathogenic bacteria and the title compound (I) is an example of one of these compounds of which previous examples have been reported (Chanawanno et al, 2010a,b;Fun et al, 2010).…”

Section: Methodsmentioning

confidence: 99%

“…

The antibacterial significance of synthetic quinolinium derivatives has been discovered by many scientists (Babalola, 1998;Collier et al, 1953;Gutsulyak, 1972). Due to these well-known bioactivities of quinolinium chemophores, our research group has designed and synthesized several quinolinium stilbene derivatives in order to investigate their ability to overcome some of Gram-positive and Gram-negative pathogenic bacteria and the title compound (I) is an example of one of these compounds of which previous examples have been reported (Chanawanno et al, 2010a,b;Fun et al, 2010).The title compound was tested for antibacterial activities against Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis, Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecalis, Salmonella typhi, Shigella sonnei and Pseudomonas aeruginosa, and it was found to be inactive (MICs against all strains were more than 300 µg/ml).

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confidence: 99%

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(E)-2-[4-(Diethylamino)styryl]-1-methylquinolinium 4-fluorobenzenesulfonate monohydrate

et al. 2013

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In the title hydrated molecular salt, C22H25N2 +·C6H4FO3S−·H2O, the cation displays whole molecule disorder over two sets of sites in a 0.780 (5):0.220 (5) ratio. The quinolinium ring system is essentially planar, with r.m.s. deviations of 0.0162 and 0.0381 Å for the major and minor disorder components, respectively. The dihedral angles between the mean plane of the quinolinium ring system and the benzene ring are 5.1 (3) and 7.7 (11)°, respectively, for the major and minor components in the cation. In the crystal, cations, anions and water molecules are linked into chains along [010] by O—H⋯O hydrogen bonds and are further connected into a three-dimensional network by weak C—H⋯O and C—H⋯F interactions. In addition, π–π interactions with centroid–centroid distances of 3.634 (3), 3.702 (5) and 3.838 (5) Å are observed.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

(E)-2-[4-(Diethylamino)styryl]-1-methylquinolinium 4-fluorobenzenesulfonate monohydrate

et al. 2013

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“…The bactericidal activity increases on going from pyridine derivatives to benzo-substituted compounds (quinoline), [5,6]. This trend persists even in condensed derivatives such as benzoquinolinium and benzoquinaldinium salts [7,8].…”

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confidence: 93%

Synthesis and antimicrobial activity of quaternary N-aryl-5,6-benzoquinaldinium derivatives

Щепина

Boiko²,

Александрова

2011

Pharm Chem J

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A series of quaternary N-aryl-5,6-benzoquinaldinium derivatives have been synthesized. Their antimicrobial activity (E. coli, S. aureus) has been tested. It was found that introduction of a new annelated benzene ring into the heterocyclic molecule (compared with quinolinium and benzoquinolinium compounds) leads to a significant increase of the antibacterial activity. Electron-withdrawing substituents in the quaternary phenyl group decrease slightly the antimicrobial effect. Since better results have been obtained for N-phenyl-5,6-benzoquinaldinium tetrafluoroborate, biological investigations were continued on the additional test cultures S. saprophyticus, Salmonella spp., Micrococcus luteus, Proteus vulgaris, Bacillus subtilis, and Candida albicans. The observation of high fungicidal activity against C. albicans was promising.

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“…Biological investigations reveal that the activity of pyridinium derivatives mainly depended on the structure of substituents on the heterocyclic ring [6]- [8]. Derivatives of benzopyridine-quinolinium salts open new horizons in drug chemistry [9]- [13]. In the 21st century, interest in new synthesis of perspective biologically active quinolinium structures even will increase [14]- [20].…”

Section: Introductionmentioning

confidence: 99%