Synthesis and Structures of Halo-Substituted Aroylhydrazones with Antimicrobial Activity

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.

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.


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.


Author(s):  
Dilek Demirezen-Yilmaz ◽  
Fatih Doğan Koca ◽  
Nurhan Ertaş-Onmaz

In this study, the powder of Allcemilla vulgaris was used in the sythesis of silver and zinc nanoparticle. Biologically synthesized nanoparticles were characterized using Scanning Electron Microscopy (SEM), Fourier transform infrared spectroscopy (FTIR), UV-Vis spectroscopy, X-ray diffraction (XRD) and Zeta potential and then evaluated for antibacterial potential using micro dilution broth method. The minimum inhibitory concentration values of AgNP were 4.25 µg/mL and 6.64 µg/ mL for Escherichia coli O157:H7 and Staphylococcus aureus, respectively. Similarly, the MIC values of ZnNP were 3.32 µg/mL and 6.25 µg/mL, respectively for Escherichia coli O157:H7 and Staphylococcus aureus.


Author(s):  
Thanuja B ◽  
Charles Kanagam

Objective: The objective of this work to evaluate the antimicrobial activities of synthesized 22’dichlorohydrobenzoin (22’CD) a new organic crystal.Methods: 22’CD a new organic crystal was grown by vapor diffusion method. Single crystals of 22’CD have been subjected to X-ray diffraction analysis to estimate the lattice parameters and the space group. The molecular structure was confirmed using Fourier transform infrared and nuclear magnetic resonance (NMR) spectral analyses. Optical behavior and thermal stability of the crystal were determined using UV-Vis spectroscopy and thermogravimetry-differential thermal analysis curves. In the present study, antimicrobial activity of 22’CD was evaluated against Escherichia coli and Bacillus subtilis was evaluated by agar well diffusion method.Results: Antibacterial activity of 22’CD was analyzed with ciprofloxacin and miconazole standard and tested against E. coli, Pseudomonas aeruginosa, Salmonella paratyphi, Klebsiella pneumonia’s, Staphylococcus aureus, Streptococcus progenies, and B. subtilis.Conclusion: The 22’CD was found to be effective against E. coli and B. subtitles.


2006 ◽  
Vol 61 (11-12) ◽  
pp. 773-776 ◽  
Author(s):  
Demet Cansaran ◽  
Didem Kahya ◽  
Ender Yurdakulol ◽  
Orhan Atakol

Abstract Six species of lichens, such as Usnea florida, Usnea barbata, Usnea longissima, Usnea rigida, Usnea hirta and Usnea subflorida, were collected from different areas of Anatolia (district of Antalya, Karabük, Çankırı, Giresun and Trabzon) in Turkey. Their usnic acid amounts in acetone extracts were determined by HPLC. In addition, antimicrobial activities of these extracts were determined against Escherichia coli (ATCC 35218), Enterococcus faecalis (RSKK 508), Proteus mirabilis (Pasteur Ens. 235), Staphylococcus aureus, Bacillus subtilis and Bacillus megaterium. It was shown that with increasing amount of usnic acid, the antimicrobial activity increased. Usnic acid contents of Usnea species varied between 0.22-6.49% of dry weight.


2016 ◽  
Vol 78 (6-8) ◽  
Author(s):  
Noor Izzatie Munira Kamaruddin ◽  
Nor Azah Mohamad Ali ◽  
Muhd Fauzi Safian ◽  
Zaidah Zainal Ariffin

Polyalthia stenopetala essential oils were extracted by hydrodistillation from the leaves and were analyzed using gas chromatography-flame ionization detector (GC-FID) and gas chromatography/mass spectrometry (GC/MS) system. Thirty one compounds were identified from the analysis. The most abundant components in the leaves oil are curzerene (37.56%) followed by viridiflorol (11.59%), germacrene B (3.77%) and aromadendrene (4.01%). The antimicrobial activity of the oil essential oils was determined with disk diffusion method and minimum inhibitory concentration (MIC) assay. Four bacteria, Staphylococcus aureus (ATCC 25923), Bacillus subtilis (ATCC 6633), Escherichia coli (ATCC 25922) Psedomonas aeruginosa (ATCC 10145) and two yeasts, Candida albicans (ATCC 10231) and Saccharomyces cerevisiae (ATCC 4098) were selected. The crude oil shows the most reactivity against B. subtilis (ATCC 6633) and C. albicans (ATCC 10231) with an inhibitory zone of 11mm. The minimum inhibitory concentration (MIC) of sample against Staphylococcus aureus (ATCC 25923), Bacillus subtilis (ATCC 6633), Escherichia coli (ATCC 25922) Psedomonas aeruginosa (ATCC 10145) and Candida albicans (ATCC 10231) in range of 0.5 mg/ml – 1.0 mg/ml which can categorized as strong.


2021 ◽  
Vol 22 (1) ◽  
pp. 74-87
Author(s):  
A.O. Oyedele ◽  
E.O. Akinkunmi

Background: Benzoic acid (BA) and salicylic acid (SA) combined are used as choice topical treatment for fungal and bacterial infections but their delivery is affected by ointment vehicle, among other factors. With aim to achieve improved release and antimicrobial activity in ointment formulation of these medicaments through selection of more efficient vehicle(s), this study comparatively evaluated prospective alternatives to thecompendium-specified base for delivery potential and relevant physical properties.Methodology: Water-sorption capacity, rheological characteristics and heat-tolerance limits of six hydrophilic bases [hydrous ointment (HO), hydrous sheabutter (HS), neat sheabutter (NS), lanolin anhydrous (LA), lanolin hydrous (LH), and emulsifying ointment (EO)] and their ointment products containing 1, 2, 3, or 6% w/w of BA or SA were determined. Drug delivery propensity of the products was evaluated by agar diffusion colorimetric assay, while their antimicrobial activities were determined by hole-in-plate agar diffusion assay against selected type organisms (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans and Candida pseudotropicalis).Results: BA was released in relatively larger quantity and demonstrated greater antimicrobial activity than SA in most bases. The released quantities of each medicament correlated directly with concentration and antimicrobial activities. The rates and extents of drug release followed a similar trend in different vehicles namely, HO > HS > NS ≥ EO > LA ≈ LH. Water number of base, ointment preparation method, viscosity, or heat-tolerance showed no influence on drug release or antimicrobial activity.Conclusion: HO and HS are better vehicles for delivery of BA and SA in ointment than EO which is the prototypical base. Keywords: Benzoic acid, Salicylic acid, Antimicrobial activity, Ointment base, Delivery factors French Title: Évaluation comparative des bases hydrophiles pour une meilleure administration d'acide benzoïque et d'acide salicylique dans une pommade antimicrobienne Contexte: L'acide benzoïque (BA) et l'acide salicylique (SA) combinés sont utilisés comme traitement topique de choix pour les infections fongiques et bactériennes, mais leur administration est affectée par le véhicule de la pommade, entre autres facteurs. Dans le but d'améliorer la libération et l'activité antimicrobienne dans la  formulation de pommade de ces médicaments grâce à la sélection de véhicules plus efficaces, cette étude a évalué comparativement des alternatives potentielles à la base spécifiée dans le compendium pour le potentiel d'administration et les propriétés physiques pertinentes.Méthodologie: Capacité de sorption de l'eau, caractéristiques rhéologiques et limites de tolérance à la chaleur de six bases hydrophiles [pommade hydratée (HO), beurre de karité hydraté (HS), beurre de karité pur (NS), lanoline anhydre (LA), lanoline hydratée (LH), et onguent émulsifiant (EO)] et leurs produits de pommade contenant 1, 2, 3 ou 6% p/p de BA ou SA ont été déterminés. La propension à l'administration de médicaments des produits a été évaluée par un essai colorimétrique de diffusion sur gélose, tandis que leurs activités antimicrobiennes ont été déterminées par un essai de diffusion sur gélose en plaque contre des organismes de type sélectionné (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans et Candida pseudotropicalis).Résultats: BA a été libéré en quantité relativement plus grande et a démontré une plus grande activité antimicrobienne que SA dans la plupart des bases. Les quantités libérées de chaque médicament étaient directement liées à la concentration et aux activités antimicrobiennes. Les taux et l'étendue de la libération de médicaments ont suivi une tendance similaire dans différents véhicules, à savoir HO> HS> NS ≥ EO> LA ≈ LH. Le nombre d'eau de base, la méthode de préparation de la pommade, la viscosité ou la tolérance à la chaleur n'ont montré aucune influence sur la libération du médicament ou l'activité antimicrobienne.Conclusion: HO et HS sont de meilleurs véhicules pour la livraison de BA et SA en onguent que EO qui est la base prototypique. Mots-clés: acide benzoïque, acide salicylique, activité antimicrobienne, base de pommade, facteurs de délivrance  


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.


2020 ◽  
Vol 15 (6) ◽  
pp. 665-679
Author(s):  
Alok K. Srivastava ◽  
Lokesh K. Pandey

Background: [1, 3, 4]oxadiazolenone core containing chalcones and nucleosides were synthesized by Claisen-Schmidt condensation of a variety of benzaldehyde derivatives, obtained from oxidation of substituted 5-(3/6 substituted-4-Methylphenyl)-1, 3, 4-oxadiazole-2(3H)-one and various substituted acetophenone. The resultant chalcones were coupled with penta-O-acetylglucopyranose followed by deacetylation to get [1, 3, 4] oxadiazolenone core containing chalcones and nucleosides. Various analytical techniques viz IR, NMR, LC-MS and elemental analysis were used to confirm the structure of the synthesised compounds.The compounds were targeted against Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and Aspergillus flavus, Aspergillus niger and Fusarium oxysporum for antifungal activity. Methods: A mixture of Acid hydrazides (3.0 mmol) and N, Nʹ- carbonyl diimidazole (3.3 mmol) in 15 mL of dioxane was refluxed to afford substituted [1, 3, 4]-oxadiazole-2(3H)-one. The resulted [1, 3, 4]- oxadiazole-2(3H)-one (1.42 mmol) was oxidized with Chromyl chloride (1.5 mL) in 20 mL of carbon tetra chloride and condensed with acetophenones (1.42 mmol) to get chalcones 4. The equimolar ratio of obtained chalcones 4 and β -D-1,2,3,4,6- penta-O-acetylglucopyranose in presence of iodine was refluxed to get nucleosides 5. The [1, 3, 4] oxadiazolenone core containing chalcones 4 and nucleosides 5 were tested to determined minimum inhibitory concentration (MIC) value with the experimental procedure of Benson using disc-diffusion method. All compounds were tested at concentration of 5 mg/mL, 2.5 mg/mL, 1.25 mg/mL, 0.62 mg/mL, 0.31 mg/mL and 0.15 mg/mL for antifungal activity against three strains of pathogenic fungi Aspergillus flavus (A. flavus), Aspergillus niger (A. niger) and Fusarium oxysporum (F. oxysporum) and for antibacterial activity against Gram-negative bacterium: Escherichia coli (E. coli), and two Gram-positive bacteria: Staphylococcus aureus (S. aureus) and Bacillus subtilis(B. subtilis). Result: The chalcones 4 and nucleosides 5 were screened for antibacterial activity against E. coli, S. aureus and B. subtilis whereas antifungal activity against A. flavus, A. niger and F. oxysporum. Compounds 4a-t showed good antibacterial activity whereas compounds 5a-t containing glucose moiety showed better activity against fungi. The glucose moiety of compounds 5 helps to enter into the cell wall of fungi and control the cell growth. Conclusion: Chalcones 4 and nucleosides 5 incorporating [1, 3, 4] oxadiazolenone core were synthesized and characterized by various spectral techniques and elemental analysis. These compounds were evaluated for their antifungal activity against three fungi; viz. A. flavus, A. niger and F. oxysporum. In addition to this, synthesized compounds were evaluated for their antibacterial activity against gram negative bacteria E. Coli and gram positive bacteria S. aureus, B. subtilis. Compounds 4a-t showed good antibacterial activity whereas 5a-t showed better activity against fungi.


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