scholarly journals Synthesis, Characterization and Crystal Structures of Fluoro-Substituted Aroylhydrazones with Antimicrobial Activity

2021 ◽  
Vol 68 (3) ◽  
pp. 541-547
Author(s):  
Fu-Ming Wang ◽  
Li-Jie Li ◽  
Guo-Wei Zang ◽  
Tong-Tong Deng ◽  
Zhong-Lu You

A series of five new fluoro-substituted aroylhydrazones were prepared and structurally characterized by elemental analysis, IR, UV-Vis and 1H NMR spectroscopy, as well as single crystal X-ray diffraction. The compounds were evaluated for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence) and antifungal (Candida albicans and Aspergillus niger) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. The biological assay indicated that the presence of the electron-withdrawing groups in the aroylhydrazones improved their antimicrobial activities.

2012 ◽  
Vol 65 (4) ◽  
pp. 343 ◽  
Author(s):  
Mei Zhang ◽  
Dong-Mei Xian ◽  
Hai-Hua Li ◽  
Ji-Cai Zhang ◽  
Zhong-Lu You

A series of new halo-substituted aroylhydrazones have been prepared and structurally characterized by elemental analysis, 1H NMR, 13C NMR, and IR spectra, and single crystal X-ray diffraction. The compounds were evaluated for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence) and antifungal (Candida albicans and Aspergillus niger) activities by the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. Among the tested compounds, N′-(2-chloro-5-nitrobenzylidene)-2-fluorobenzohydrazide showed the most effective antimicrobial activity with minimum inhibitory concentration values of 0.82, 2.5, 1.7, 15.2, and 37.5 μg mL–1 against B. subtilis, S. aureus, E. coli, P. fluorescence, and C. albicans, respectively. The biological assay indicated that the presence of the electron-withdrawing groups in the aroylhydrazones improved their antimicrobial activities.


2012 ◽  
Vol 61 (3) ◽  
pp. 223-225
Author(s):  
MUHAMMAD JAWWAD SAIF ◽  
MOHAMMED ZUBER ◽  
JAMIL ANWAR ◽  
MUNAWAR ALI MUNAWAR

The antimicrobial activity of two new series of bis-piperidinium compounds with alkyl chains of different lengths against bacterial (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis) and fungal strains (Aspergillus flavus, Aspergillus niger, Rhodolorula rubera, Lipomyces lopofera and Candida albicans), are described. Antimicrobial activities of the synthesized compounds were compared to that of dodecyltrimethylammonium chloride. Bis-piperidinium salts possessing 12-16 carbon side chains showed better antimicrobial properties as compared to the standard dodecyltrimethylammonium chloride.


2018 ◽  
Vol 13 (4) ◽  
pp. 1934578X1801300
Author(s):  
Daniyar Sadyrbekov ◽  
Timur Saliev ◽  
Yuri Gatilov ◽  
Ivan Kulakov ◽  
Roza Seidakhmetova ◽  
...  

A cyclopropane derivative of limonene, (1 S, 4 S, 6 R)-7,7-dichloro-4-[(1 S)-2,2-dichloro-1-methylcyclopropyl]-1-methylbicyclo [4.1.0] heptane (compound 2), was synthesized and its structure was determined by NMR and X-ray crystallographic methods. In addition, an antimicrobial activity of the compound against Gram-positive ( Staphylococcus aureus, Bacillus subtilis) and Gram-negative ( Escherichia coli, Pseudomonas aeruginosa) bacterial strains was also scrutinized.


Medicina ◽  
2008 ◽  
Vol 44 (12) ◽  
pp. 977 ◽  
Author(s):  
Alvydas Pavilonis ◽  
Algirdas Baranauskas ◽  
Ligita Puidokaitė ◽  
Žaneta Maželienė ◽  
Arūnas Savickas ◽  
...  

Objective. To evaluate the antimicrobial activity of soft and purified propolis extracts. Study object and methods. Antimicrobial activity of soft and purified propolis extracts was determined with reference cultures of Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 33499, Pseudomonas aeruginosa ATCC 27853, Proteus mirabilis ATCC 12459, Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 8035, and fungus Candida albicans ATCC 60193. Microbiological tests were performed under aseptic conditions. Minimum inhibitory concentration (MIC) – the highest dilution of preparation (the lowest concentration of preparation) that suppresses growth of reference microorganisms – was determined. Results. Concentration of phenolic compounds in soft propolis extract that possesses antimicrobial activity against gram-positive (Staphylococcus aureus, Enterococcus faecalis) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Proteus mirabilis) is 0.587±0.054 mg and 0.587±0.054–0.394±0.022 mg (P>0.05) and in purified propolis extract – 0.427±0.044 mg and 0.256±0.02 mg (P>0.05). Klebsiella pneumoniae is most resistant to soft propolis extract when the concentration of phenolic compounds is 1.119± 0.152 mg and to purified propolis extract when the concentration of phenolic compounds is 1.013±0.189 mg (P>0.05). Spore-forming Bacillus subtilis bacteria are more sensitive to soft and purified propolis extracts when the concentration of phenolic compounds is 0.134±0.002 mg and 0.075±0.025 mg, respectively, and Bacillus cereus – when the concentration is 0.394±0.022 mg and 0.256±0.02 mg (P>0.05). Sensitivity of fungus Candida albicans to soft and purified propolis extracts is the same as Bacillus subtilis. Encapsulated bacterium Klebsiella pneumoniae is most resistant to antimicrobial action of soft and purified propolis extracts as compared with gram-positive Staphylococcus aureus and Enterococcus faecalis bacteria (P<0.05), gram-negative Escherichia coli, Pseudomonas aeruginosa, and Proteus mirabilis (P<0.05), sporeforming Bacillus subtilis and Bacillus cereus bacteria (P<0.05), and fungus Candida albicans (P<0.05). There is no statistically significant difference between antimicrobial effect of soft propolis extract and purified propolis extract on gram-positive bacteria, gram-negative bacteria, spore-forming bacteria, encapsulated bacteria, and Candida fungus. Conclusions. Soft and purified propolis extracts possess antimicrobial activity. They could be recommended as natural preservatives in the manufacture of pharmaceutical products.


1994 ◽  
Vol 302 (2) ◽  
pp. 535-538 ◽  
Author(s):  
J Alvarez-Bravo ◽  
S Kurata ◽  
S Natori

Previously, we identified a core undecapeptide of sapecin B having antimicrobial activity. Based on the structure of this peptide, we systematically synthesized peptides consisting of terminal basic motifs and internal oligo-leucine sequences and examined their antimicrobial activities. Of these peptides, RLKLLLLLRLK-NH2 and KLKLLLLLKLK-NH2 were found to have potent microbicidal activity against Staphylococcus aureus, Escherichia coli, methicillin-resistant S. aureus and Candida albicans in liquid medium. We also synthesized the D-enantiomer of KLKLLLLLKLK-NH2. This enantiomer was resistant to tryptic digestion and persisted longer in the culture medium, showing greater antimicrobial activity than the original peptide.


Medicina ◽  
2011 ◽  
Vol 47 (3) ◽  
pp. 24 ◽  
Author(s):  
Vilma Jurkštienė ◽  
Alvydas Pavilonis ◽  
Daiva Garšvienė ◽  
Algirdas Juozulynas ◽  
Laimutė Samsonienė ◽  
...  

The aim of the study was to determine antimicrobial activity of rhaponticum and shrubby cinquefoil extracts. Material and Methods. Ethanol extract from the leaves of rhaponticum (Rhaponticum carthamoides D.C. Iljin) and shrubby cinquefoil (Potentilla fruticosa L.) was produced at the Department of Food Technology, Kaunas University of Technology. The antimicrobial activity of the viscous extract or rhaponticum and shrubby cinquefoil was evaluated using standard microorganism cultures (bacteria Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 33499, Pseudomonas aeruginosa ATCC 27853, Proteus mirabilis ATCC 12459, Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 8035 and fungi Candida albicans ATCC 60193). The minimum inhibitory concentration (MIC) of the examined preparations was determined. Results. Both studied preparations – rhaponticum (Rhaponticum carthamoides D.C. Iljin) and shrubby cinquefoil (Potentilla fruticosa L.) – demonstrated similar antimicrobial activity. The highest sensitivity to the studied preparations was observed in microbes with eukaryotic cell structure: Candida albicans, which is a fungus, and a spore-forming prokaryotic bacterium, Bacillus cereus. The highest resistance was observed in Escherichia coli and Klebsiella pneumoniae. Conclusions. The studied preparations – viscous extracts of rhaponticum and shrubby cinquefoil – are substances with antimicrobial activity against gram-positive (Staphylococcus aureus and Enterococcus faecalis) and gram-negative (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Proteus mirabilis) bacteria, spore-forming bacteria (Bacillus subtilis and Bacillus cereus), and fungi (Candida albicans).


2021 ◽  
Vol 47 (3) ◽  
pp. 1296-1302
Author(s):  
Oluwaseyi B. Ovonramwen ◽  
Bodunde J. Owolabi ◽  
Abiodun Falodun

A new 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide was synthesized from methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate and ethylamine. The compound methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate was synthesized from methyl pyrrolidine-2-carboxylate and 5-chloro-4-chlorosulfonyl-1-ethyl-2-methyl-imidazole. The compounds were characterized based on FTIR, 1H, 13C NMR, and DEPT 135 analysis. Antimicrobial activities of the 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae), and Candida albicans were carried out using the standard microbiological method. The newly synthesized 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide had no activities against the tested organisms. Keywords:    1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide; methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate; L-proline; ethylamine.


2005 ◽  
Vol 60 (1-2) ◽  
pp. 35-38 ◽  
Author(s):  
Meral Yılmaz ◽  
Turgay Tay ◽  
Merih Kıvanç ◽  
Hayrettin Türk ◽  
Ayşen Özdemir Türk

The antimicrobial activity and the MIC values of the diethyl ether, acetone, chloroform, petroleum ether, and ethanol extracts of the lichen Hypogymnia tubulosa and its 3-hydroxyphysodic acid constituent have been investigated against some microorganisms. At least one of the extracts or 3-hydroxyphysodic acid showed antimicrobial activity against Aeromonas hydrophila, Bacillus cereus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, Listeria monocytogenes, Proteus vulgaris, Salmonella typhimurium, Staphylococcus aureus, Streptococcus faecalis, and Candida albicans. No antifungal activity of the extracts has been observed against ten filamentous fungi.


2010 ◽  
Vol 59 (1) ◽  
pp. 49-53 ◽  
Author(s):  
BOGUMIŁ BRYCKI ◽  
ZOFIA DEGA-SZAFRAN ◽  
ILONA MIRSKA

The synthesis and antimicrobial activity of 31 morpholinium chlorides, divided into five series depending on the substituents attached to the nitrogen atom, N-carboxyalkyl-morpholinium chlorides (1a-e), N-carbalkoxymethyl-N-methyl-morpholinium chlorides (2a-f), N-carbethoxymethyl-N-alkyl-morpholinium chlorides (3a-g), N-carbalkoxymethyl-N-dodecyl-morpholinium chlorides (4a-f) and N-carboxymethyl-N-alkyl-morpholinium chlorides (5a-g) is reported. The compounds investigated were tested for antimicrobial activity against Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa, Candida albicans and Trichophyton menthagrophytes. The most active are compounds with a long N-alkyl group and with the substituent CH2COOC(n)H(2n-1) (n = 8-16).


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