scholarly journals One-pot synthesis of carbazole based 3-hydroxy-4H-chromen-4-ones by modified Algar-Flynn-Oyamada reaction and their antimicrobial activity

2015 ◽  
Vol 80 (11) ◽  
pp. 1361-1366 ◽  
Author(s):  
Dongamanti Ashok ◽  
Sidda Ravi ◽  
Vijaya Lakshmi ◽  
Arram Ganesh

A new series of 2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-4Hchromen-4-ones have been synthesized from substituted 2-hydroxy acetophenones and 9-ethyl-9H-carbazole-3-carbaldehyde using NaOH and H2O2 by modified Algar-Flynn-Oyamada reaction. In this method flavonols are synthesized without isolating chalcones in good yields (70-82%). The structures of the compounds were established on the basis of 1H-NMR, 13CNMR, FT-IR and mass spectral and analytical data. All the compounds were evaluated for their antimicrobial activity against bacteria such as Staphylococus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae as well as fungi such as Aspergillus flavus and Fusarium oxysporum.

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.


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).


Author(s):  
Powar Priyatama V ◽  
Powar Trupti A

The growing phenomenon of antibiotic resistance, particularly to pathogenic microorganisms, in current medicine, has directed the concern of scientists for finding novel antimicrobial agents from plant origin with negligible side effect. The present study was aimed to phytochemical investigation and antimicrobial activity of seed extract of Datura stramonium in sequentially with different organic solvents. For this, antimicrobial properties were tested against bacteria Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumonia and Bacillus subtilis by cup plate method. Among the tested bacterial Klebsiella pneumoniae was the most inhibited majorly with the chloroform extract. Datura stramonium chloroform seed extract produced maximum zone of inhibition 26 mm against Klebsiella pneumoniae and 12 mm against Bacillus subtilis and 13 mm against Escherichia coli. Datura Stramonium methanol seed extract produced maximum zone of inhibition 27 mm against Pseudomonas aeruginosa and 15 mm against Bacillus subtilis, 14 mm against Staphylococcus aureus and 19 mm against Escherichia coli. Datura stramonium petroleum ether seed extract produced 16 mm zone of inhibition against Escherichia coli. Datura stramonium aqueous seed extract exhibits 24 mm zone of inhibition against Bacillus subtilis. All the experienced solvent extracts showed potential antimicrobial activity Index against various tested microorganisms. Owning to the results, it can be concluded that the extracts of the Datura stramonium can be used to design different herbal antimicrobial agents.


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.


2021 ◽  
Vol 5 (4) ◽  
pp. 220-227
Author(s):  
Oksana Mykchaylova ◽  
Nataliia Poyedіnok

Background. According to the World Health Organization antibiotic resistance is among the top ten threats to human health, food safety and development. Today antibiotic resistance has reached alarmingly high levels all over the world. Meanwhile, the increase in the synthetic drugs' production has led to the pathogenic mycobiota's rapid adaptation to the created chemicals, which have a narrow focus of application. That is why in modern biotechnology and pharmacology much attention is paid to natural producers of biologically active compounds, in particular – to xylotrophic fungi. It has been experimentally proven that the xylotrophic macromycete Fomitopsis officinalis or tinder fungus can be considered to be a promising producer of pharmacological substances with a broad spectrum of action. Studies of active metabolites, contained in the mycelial mass, culture fluid of the medicinal xylotrophic macromycete F. officinalis, and determination of their biological action remain relevant. Objective. The objective was to determine the antimicrobial activity of culture fluid and mycelial mass of F. officinalis different strains from the mushrooms collection (IBK Mushroom Culture Collection of the M.G. Kholodny Institute of Botany, NAS of Ukraine) against gram-negative and gram-positive bacteria species. Methods. An in vitro study of the antimicrobial activity of ethyl acetate extracts of culture fluid and aqueous-ethyl extracts of mycelial mass for F. officinalis strains IBK-5004, IBK-2497, IBK-2498 against gram-positive Staphylococcus aureus (B-918), Bacillus subtilis (В-901) and gram-negative Escherichia coli (B-906), Bacillus subtilis (B-900), Klebsiella pneumoniae (M-123) bacteria by disc-diffusion method was conducted. Results. High antimicrobial activity of tinder fungus culture fluid and mycelial mass extracts against Staphylococcus aureus was established after the 21st day of cultivation, while on the 28th day the zone of growth retardation was maximal (15–25 mm). The highest indices were recorded in F. officinalis IBK-5004 (20–25 mm) and IBK-2498 (20–24 mm) strains. Antimicrobial activity against Klebsiella pneumoniae in culture fluid extracts was manifested on the 21st and 28th days of cultivation. The highest antimicrobial activity against Klebsiella pneumoniae was observed in the culture fluid of the strain F. officinalis IBK-5004, the diameter of the growth retardation zone was 18 mm on the 28th day of cultivation. Mycelial mass's extracts showed moderate activity on the 14th day of cultivation (7-8 mm); maximal activity was recorded on the 28th day (12–22 mm). The most active strain was Fomitopsis officinalis IBK-2498. No antimicrobial activity against test organisms was detected in the following studied strains: Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis. Conclusions. It has been established that the mycelial mass and culture fluid extracts of F. officinalis IBK-5004, IBK-2497, IBK-2498 strains have high antimicrobial activity against Staphylococcus aureus and moderate antimicrobial activity against Klebsiella pneumoniae on the 21st and 28th day of cultivation.


Author(s):  
Suzana . ◽  
Isnaeni . ◽  
Tutuk Budiati

In this study, synthesized N'-(2-methoxybenzylidene)-4-hydroxybenzohydrazide and N'-(4-nitrobenzylidene)-4- hydroxybenzohydrazide in two step reaction by using methylparaben as starting material has been performed. Methylparaben was treated with hydrazine hydrate to obtain 4-hydroxybenzohydrazide. The reaction was carried out by microwave irradiation resulting 91 % yield. The obtained compound was then reacted with 2-methoxbenzaldehyde or 4- nitrobenzaldehyde to accomplish the target molecule, N'-(2-methoxybenzylidene)-4-hydroxybenzohydrazide and N'-(4- nitrobenzylidene)-4-hydroxybenzohydrazide in 55% and 72% yield respectively. Identification of N'-(2- methoxybenzylidene)-4-hydroxy benzo hydrazide and N'-(4-nitrobenzylidene)-4-hydroxybenzohidroksida was performed by FT-IR, MS, 1H-NMR, and 13C-NMR spectroscopy. In silico study was done with receptor pdb 1C14. The N'-(4- nitrobenzylidene)-4-hydroxybenzohydrazide exhibited antimicrobial activity against Escherichia coli (MIC=31.3 ppm), Bacillus subtilis (MIC=500 ppm). Antimicrobial activity of N'-(2-methoxybenzylidene)-4-hydroxybenzohydrazide against Bacillus subtilis (MIC=31.3 ppm) and MIC= 500 ppm against Escherichia coli.


2020 ◽  
Vol 17 (12) ◽  
pp. 1538-1551
Author(s):  
Nadia Ali Ahmed Elkanzi ◽  
Rania Badaway Bakr

Background: Pyrimidine ring is one of the most important heterocyclic scaffolds due to its biological benefits as antimicrobial agents via acting as competitive suppressors of dihydropteroate synthase (DHPS) enzyme, inhibiting dihydrofolate reductase or glucosamine N-phosphate synthase. Objective: The objective of this work is preparing twenty four derivatives of pyrimidine heterocycle 1a-f, 2a-f, 3a-f and 4a-f via a facile one step reaction with antimicrobial potential. Methods: Novel twenty four derivatives of pyrimidine heterocycle 1a-f, 2a-f, 3a-f and 4a-f were prepared via a facile one step reaction by treating substituted aldehydes, urea and / or thiourea and active methylene derivatives (diethyl malonate and / or ethyl cyanoacetate) using 1,4- diazabicyclo[2.2.2]octane (DABCO) as a basic catalyst. The chemical structures of all these novel targets were proved by 1HNMR, 13CNMR, MS and elemental analyses. All the twenty four new targets 1a-f, 2a-f, 3a-f and 4a-f were assessed for their antimicrobial activity towards bacteria as Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli and against fungi represented by Aspergillus flavus and Candida albicans. Results: Most of the compounds exhibited very good antimicrobial activity, especially; compound (1c) exhibited the most activity against three types of bacteria Escherichia coli, Bacillus subtilis, Staphylococcus aureus. Moreover, this derivative 1c displayed similar antifungal activity towards Candida albicans as that exhibited by amphotericin B. Conclusion: All the screened compounds 1a-f, 2a-f, 3a-f and 4a-f showed antibacterial activity with inhibition zone diameter range 6-21 mm/mg, while, regarding the antifungal activity, all the novel derivatives except 2b, 2d, 3a, 3c, 3e did not have any effect towards Aspergillus flavus and 3d did not reveal any inhibitory activity towards both fungal species.


Author(s):  
Zehra Edis ◽  
Samir Haj Bloukh ◽  
Hamed Abu Sara

New antibacterial agents are needed to overcome the increasing number of infectious diseases caused by pathogenic microorganisms due to the emergence of multi-drug resistant strains. &nbsp;In this context, halogens, especially Iodine is known since ages for its antimicrobial activity. Therefore, especially triiodides encapsulated in organometallic complexes can be helpful as new agents against microorganisms. The aims of this work was to study the biological activity of [Na(12-Crown-4)2]I3 against gram positive Streptococcus pyogenes, Streptococcus faecalis, the spore forming bacteria Bacillus subtilis and gram negative bacteria Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa and Klebsiella pneumoniae, as well as the yeast Candida albicans. The antimicrobial and antifungal activities of the triiodide were determined by zone of inhibition plate studies. [Na(12-Crown-4)2]I3 exhibited potent antimicrobial activity on gram positive Streptochocci and the yeast C. albicans. Furthermore, the gram negative bacteria P. aeruginosa and K. pneumoniae were less effectively inhibited, while E. coli and P. mirabilis proved to be even resistant.


2019 ◽  
Author(s):  
Chem Int

Novel acyclic and cyclic merocyanine dyes derived from the nucleu of furo [(3,2-d) pyrazole; ( d 2 , 3 )imidazole]were prepared. The electronic visible absorptionspectra of all the synthesized new cyanine dyes were examined in 95% ethanolsolution to evaluate their photosensitization properties. Antibacterial andantifungal activities for some selected dyes were tested against various bacterialand fungal strains (Escherichia coli, Staphylococcus aureus, Aspergillus flavus andCandida albicans) to evaluate their antimicrobial activity. Structural identificationwas carried out via elemental analysis, visible spectra, IR and 1H NMRspectroscopic data.


Author(s):  
Devidas G. Anuse ◽  
Suraj N. Mali ◽  
Bapu R. Thorat ◽  
Ramesh S. Yamgar ◽  
Hemchandra K. Chaudhari

Background: Antimicrobial resistance is major global health problem, which is being rapidly deteriorating the quality of human health. Series of substituted N-(benzo[d]thiazol-2-yl)-2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)acetamide (3a-j) were synthesized from substituted N-(benzo[d]thiazol-2-yl)-2-chloroacetamide/bromopropanamide (2a-j) and 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole (2) and further evaluated for their docking properties and antimicrobial activity. Methods: All synthesized compounds were characterized by FT-IR, NMR and Mass spectral analysis. All compounds were allowed to dock against different antimicrobial targets having PDB ID: 1D7U and against common antifungal target having PDB ID: 1EA1. Results: The compounds 3d and 3h were showed good activity against Methicillin-resistant Staphylococcus aureus (MRSA, resistance Gram-positive bacteria). All synthesized compounds showed good to moderate activity against selected bacterial and fungal microbial strains. If we compared the actual in-vitro antimicrobial activity and in-silico molecular docking study, we found that molecules 3i and 3h were more potent than the others. Conclusion: Our current study would definitely pave the new way towards designing and synthesis of more potent 2-aminobenzothiazoles derivatives.


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