scholarly journals Synthesis, Characterization and Antibacterial Activity of 2-Phenylsulphonamide Derivatives of Some Amino Acids

Author(s):  
Chinyere Benardette Chinaka Ikpa ◽  
Uchechukwu C. Okoro ◽  
Collins I. Ubochi ◽  
Kieran O. Nwanorh

The 2-phenylsulphonamide derivatives of amino acids were synthesis by simple substitution of benzenesulphonylchloride (6) with amino acids (1-5) containing pharmacological active functionalities. Structures of the synthesised compounds (7a-7e) were characterised using FT-IR, NMR(1H,13C) and elemental analysis. The anti bacterial activities of the synthesised compounds were evaluated against gram positive bacteria: Staph and Streptococcus, gram negative bacteria: E-coli, Klebsiella, Proteus, and pseudomonas using 200 µl of 10 mg/ml and minimum inhibitory concentration (MIC) were also determined. The compounds exhibited effective anti bacterial properties though some are not more active than the standard drug ciprofloxacin.

2019 ◽  
Vol 32 (2) ◽  
pp. 381-384
Author(s):  
G. Venkateshappa ◽  
P. Raghavendra Kumar ◽  
Krishna2

This paper reports the synthesis, characterization and antibacterial activity of N-2-(4-chlorophenyl)acetyl derivatives of various (S)-amino acids such as (S)-alanine, (S)-phenylalanine, (S)-leucine, (S)-methionine, (S)-proline and (S)-tryptophane. These compounds have been successfully synthesized and their structures were confirmed by 1H NMR and 13C NMR and FT-IR spectroscopy. The antimicrobial activity of these six (S)-amino acids derivatives have been evaluated by the agar well diffusion method against pathogens both Gram-positive (S. aureus) and Gram-negative (K. aerogenes, E. coli and P. desmolyticumas) bacteria and fungi (A. flavus and C. albicans). All these compounds have shown mild to moderate antimicrobial activity.


2020 ◽  
Vol 15 (2) ◽  
pp. 52-58
Author(s):  
Isaac Asusheyi Bello ◽  
Isaac Asusheyi Bello ◽  
George Iloegbulam Ndukwe ◽  
Joseph Olorunju Amupitan ◽  
Rachael Gbekele Ayo ◽  
...  

Structural modification of the C-9154 antibiotic in an attempt to simultaneously improve its activity and lower its toxicity led to the synthesis of an analogue of the C-9154 antibiotic and six derivatives of this analogue. The significant reduction of the polarity of the synthesized analogue in the derivatives to increase permeability across cell membranes was achieved by conversion of the highly polar carboxylic group to the nonpolar ester functional groups. The compounds were synthesized by condensation of 4-nitroaniline with maleic anhydride and then conversion of the terminal carboxylic acid functional group to an ester functional group using a thionyl chloride-mediated esterification. The in vitro biological activity using gram positive bacteria (MRSA, S. pyogenes, B. subtilis, and C. ulcerans), gram negative bacteria (E. coli, P. mirabilis, P. aeruginosa, S. typhii, S. dysenteriae, and K. pneumonia and some fungi (C. albicans, A. nigre and T. rubrum), showed that the derivatives were more active than their respective analogue and significantly better than the standard antibiotics (Sparfloxacin and Fluconazole) used for comparison, establishing their potential or use as antibiotics. The derivatives exhibited activity at concentrations as low as 0.625μg/mL while the analogue was active at 2.5μg/mL. These values were higher than results obtained for the standard drugs which showed activity at concentrations of 5 μg/mL. The derivatives however did not show activity against A. nigre whereas the analogue was active against it. Keywords: C-9154 Antibiotic, Bioactivity, Fumaramidmycin, antibacterial, antifungal


2021 ◽  
pp. 1330-1341
Author(s):  
Mbarga M. J. Arsène ◽  
I. V. Podoprigora ◽  
Anyutoulou K. L. Davares ◽  
Marouf Razan ◽  
M. S. Das ◽  
...  

Background and Aim: The gradual loss of efficacy of conventional antibiotics is a global issue. Plant material extracts and green-synthesized nanoparticles are among the most promising options to address this problem. Therefore, the aim of this study was to assess the antibacterial properties of aqueous and hydroalcoholic extracts of grapefruit peels as well as their inclusion in green-synthesized silver nanoparticles (AgNPs). Materials and Methods: Aqueous and hydroalcoholic extracts (80% v/v) were prepared, and the volume and mass yields were determined. The synthesis of AgNPs was done in an eco-friendly manner using AgNO3 as a precursor. The nanoparticles were characterized by ultraviolet–vis spectrometry and photon cross-correlation spectroscopy. The antibacterial activity of the extracts was tested on three Gram-positive bacteria (Staphylococcus aureus ATCC 6538, clinical Enterococcus faecalis, and S. aureus) and two Gram-negative bacteria (two clinical Escherichia coli) using various concentrations of extracts (100, 50, 25, 12, and 5 mg/mL and 5% dimethyl sulfoxide as negative control). Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined using the microdilution method. Modulation of cefazoline and ampicillin on resistant E. coli and S. aureus strains was added to the mixture design response surface methodology with extreme vertices design, with the diameters of inhibition and the fractional inhibitory concentration index as responses and factors, respectively. The antibiotic, the ethanolic extract, and water varied from 0.1 MIC to 0.9 MIC for the first two and from 0 to 0.8 in proportion for the third. Validating the models was done by calculating the absolute average deviation, bias factor, and accuracy factor. Results: The volume yield of the EE and aqueous extract (AE) was 96.2% and 93.8% (v/v), respectively, whereas their mass yields were 7.84% and 9.41% (m/m), respectively. The synthesized AgNPs were very uniform and homogeneous, and their size was dependent on the concentration of AgNO3. The antibacterial activity of the two extracts was dose-dependent, and the largest inhibition diameter was observed for the Gram-positive bacteria (S. aureus ATCC 6538; AE, 12; EE, 16), whereas AgNPs had a greater effect on Gram-negative bacteria. The MICs (mg/mL) of the AEs varied from 3.125 (S. aureus ATCC 6538) to 12.5 (E. coli 1 and E. coli 2), whereas the MICs of the EEs varied from 1.5625 (S. aureus 1, S. aureus ATCC 6538, and E. faecalis) to 6.25 (E. coli 1). There was a significant difference between the MICs of AEs and EEs (p=0.014). The MBCs (mg/mL) of the AEs varied from 12.5 (S. aureus ATCC 6538) to 50 (S. aureus 1), whereas those of the EEs varied from 6.25 (S. aureus 1) to 25 (E. coli 1 and E. faecalis). Ethanolic grapefruit extracts demonstrated an ability to modulate cefazolin on E. coli and S. aureus but were completely indifferent to ampicillin on E. coli. Conclusion: Grapefruit peel extracts and their AgNPs exhibit antibacterial properties that can be exploited for the synthesis of new antimicrobials and their EEs may be efficiently used synergistically with other antibiotics against bacteria with intermediate susceptibility.


2020 ◽  
Vol 16 (4) ◽  
pp. 481-488
Author(s):  
Heli Sanghvi ◽  
Satyendra Mishra

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.


2008 ◽  
Vol 63 (10) ◽  
pp. 1223-1230 ◽  
Author(s):  
Imran Sajid ◽  
Khaled A. Shaaban ◽  
Holm Frauendorf ◽  
Shahida Hasnain ◽  
Hartmut Laatscha

AbstractVal-Geninthiocin (2), a new member of thiopeptide antibiotics, was isolated from the mycelium of Streptomyces sp. RSF18, along with the closely related geninthiocin (1) and the macrolide, chalcomycin. By intensive NMR and MS studies, Val-geninthiocin (2) was identified as desoxygeninthiocin, a thiopeptide, containing several oxazole and thiazole units and a number of unusual amino acids. Compound 2 shows potent activity against Gram-positive bacteria and minor antifungal activity, while it is not effective against Gram-negative bacteria or microalgae. Here we describe the fermentation, isolation and structure elucidation as well as the biological activity of 2.


2020 ◽  
Vol 7 (8) ◽  
pp. 1290
Author(s):  
Saswat Subhankar ◽  
K. Madhuri ◽  
Vivek D. Alone

Osteomyelitis is an infection of the bones caused by pyogenic organisms. The ribs are an extremely uncommon site for osteomyelitis, occurring in less than 1% cases. The main causative organisms are Gram-positive bacteria, such as Staphylococcus aureus and Hemophilus influenzae. Gram-negative bacteria like E. coli have been rarely reported. Authors hereby present a case of an immune-competent patient who presented with an osteomyelitis of the ribs caused by the latter. In developing countries, tuberculosis is considered as the primary cause of osteomyelitis and pleural effusions. However, other organisms should also be considered in patients who present with fulminant infections.


1996 ◽  
Vol 34 (10) ◽  
pp. 89-95 ◽  
Author(s):  
Hu Tai-Lee

The use of biomass for the removal of reactive dyes from an aqueous solution with different bacterial genera has been investigated. Three Gram-negative bacteria: Aeromonas sp., P. luteola and E. coli, and two Gram-positive bacteria: B. subtilis and S. aureus and a mixed biomass of activated sludge are the tested biosorbents. Dead cells of Gram-negative bacteria have a higher specific adsorption capacity than the living cells. The dye removal is in the order of Aeromonoas sp. > P. luteola > E. coli. The adsorption equilibrium can be reached within one hour. Due to the positively charged cells at acidic pH, the removal of reactive dyes increases with decreasing pH. Evaluating the adsorption parameters, bacterial biomass exhibits stable adsorption characteristics, which makes it a suitable adsorbent for different dye compounds.


2019 ◽  
Vol 18 (5) ◽  
pp. 1147-1155 ◽  
Author(s):  
Rehan Khan ◽  
Melis Özkan ◽  
Aisan Khaligh ◽  
Dönüs Tuncel

Water-dispersible glycosylated poly(2,5′-thienylene)porphyrin-based nanoparticles have the ability to generate singlet oxygen in high yields and exhibit light-triggered antibacterial activity against Gram negative bacteria, E. coli as well as Gram positive bacteria, B. subtilis.


2020 ◽  
Vol 840 ◽  
pp. 265-269
Author(s):  
Nurjanah Nurjanah ◽  
Endang Saepudin

Curcumin, a diarylheptanoids compound which isolated primary from Curcuma longa, exhibits a variety of exciting biological activities, including as an antibacterial agent. In the present study, a sulfanilamide-contained curcumin compound was synthesized and characterized to investigate the antibacterial activity against gram-positive bacteria S. aureus, B. subtilis and gram-negative bacteria E. coli. The characterization of the synthesized compound was determined by analysing peak absorbance, functional group, and molecular weight using mass spectroscopy, UV/Vis and FTIR spectrophotometry. Curcumin-sulfanilamide compound exhibited the best antibacterial activity against gram-negative bacteria compared to curcumin and the curcumin-derived compound containing isoxazole with inhibitory zone of 11 mm.


2005 ◽  
Vol 2 (2) ◽  
pp. 109-112
Author(s):  
A. K. Parekh ◽  
K. K. Desai

Some new chalcones have been prepared by Claisen-schmidt condensation of ketone and different aromatic aldehydes. These chalcones on condensation with urea in presence of acid gave Pyrimidine-2-ones. The synthesized compounds have been characterized by elemental analysis, IR and1H NMR spectral data. They have been screened for their antibacterial activity against Gram positive bacteria B. subtillis & S. aureus and Gram negative bacteria E. coli & S. typhi.


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