Synthesis, antimicrobial and antifungal activity of double quaternary ammonium salts of biphenyls

Ol’khovik, V. K.; Matveienko, Yu. V.; Vasilevskii, D. A.; Kalechits, G. V.; Zheldakova, R. A.

doi:10.1134/s1070363213020163

Cited by 6 publications

(4 citation statements)

References 2 publications

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“…In agreement with these data, the TTC application as indicator for the antibacterial activity proved to be an efficient evaluation method of bacteria viability [38,39]. In few papers, the antimicrobial activity of QAs and their derivatives have also been suggested [24,38,40]. The antibacterial action of QAs consisted disruption of lipid membrane through association of the positively charged quaternary nitrogen with the polar head groups of acidic phospholipids [31,41].…”

Section: Resultsmentioning

confidence: 91%

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

et al. 2019

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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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Section: Resultsmentioning

confidence: 91%

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

et al. 2019

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“…Biphenyl derivatives which are used to produce an extensive range of drugs, products for agriculture, uorescent layers in organic lightemitting diodes (OLEDs) 5,6 and building blocks for basic liquid crystals are signicant intermediates in organic chemistry besides being the structural moiety of an extensive range of compounds with pharmacological activities. [7][8][9][10] Whereas several biphenyl derivatives serve as versatile and multifaceted platforms in medicinal chemistry, as large number of biphenyl derivatives are patented and broadly used in medicine as the antiandrogenic, 11 immunosuppressant, antifungal, antibacterial, antimicrobial, anti-inammatory, anti-proliferative, osteoporosis, antihypertensive, antitumor, b-glucuronidase inhibition activity, anti-leukemia agent hypotensive, anticholinesterase, anti-diabetic and antimalaria drugs. 12 In addition, 6-(3-(adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid which trademark drug (adapalene) as a third-generation topical retinoid primarily used for treating acne vulgaris, anti-inammatory, antibacterial.…”

Section: Introduction and Scopementioning

confidence: 99%

A fruitful century for the scalable synthesis and reactions of biphenyl derivatives: applications and biological aspects

et al. 2023

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“…However, the low solubility of biphenyl compounds in both water and common organic solvents is a major drawback which impedes their synthesis and development for pharmaceutical applications. To address this issue, Ol'khovik et al incorporated the quaternary ammonium group in the development of antimicrobial biphenyl molecules [49].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Biphenylglyoxamide-Based Small Molecular Antimicrobial Peptide Mimics as Antibacterial Agents

Kuppusamy

Yasir

et al. 2020

IJMS

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There has been an increasing interest in the development of antimicrobial peptides (AMPs) and their synthetic mimics as a novel class of antibiotics to overcome the rapid emergence of antibiotic resistance. Recently, phenylglyoxamide-based small molecular AMP mimics have been identified as potential leads to treat bacterial infections. In this study, a new series of biphenylglyoxamide-based small molecular AMP mimics were synthesised from the ring-opening reaction of N-sulfonylisatin bearing a biphenyl backbone with a diamine, followed by the conversion into tertiary ammonium chloride, quaternary ammonium iodide and guanidinium hydrochloride salts. Structure–activity relationship studies of the analogues identified the octanesulfonyl group as being essential for both Gram-positive and Gram-negative antibacterial activity, while the biphenyl backbone was important for Gram-negative antibacterial activity. The most potent analogue was identified to be chloro-substituted quaternary ammonium iodide salt 15c, which possesses antibacterial activity against both Gram-positive (MIC against Staphylococcus aureus = 8 μM) and Gram-negative bacteria (MIC against Escherichia coli = 16 μM, Pseudomonas aeruginosa = 63 μM) and disrupted 35% of pre-established S. aureus biofilms at 32 μM. Cytoplasmic membrane permeability and tethered bilayer lipid membranes (tBLMs) studies suggested that 15c acts as a bacterial membrane disruptor. In addition, in vitro toxicity studies showed that the potent compounds are non-toxic against human cells at therapeutic dosages.

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Synthesis, antimicrobial and antifungal activity of double quaternary ammonium salts of biphenyls

Cited by 6 publications

References 2 publications

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

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

A fruitful century for the scalable synthesis and reactions of biphenyl derivatives: applications and biological aspects

Design, Synthesis and Biological Evaluation of Biphenylglyoxamide-Based Small Molecular Antimicrobial Peptide Mimics as Antibacterial Agents

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