Design, Molecular Docking, Synthesis and Biological Evaluation of 4, 5-Substituted 1, 2, 3-Triazoles as Anti-bacterial Agents

2021 ◽  
Vol 14 (2) ◽  
pp. 5372-5383
Author(s):  
Vijayabhargavi M ◽  
Kusuma M. P. ◽  
Akhila Sai ◽  
Sumakanth M ◽  
Zaber Unnisa
Keyword(s):  
Antibacterial Activity ◽  
Bacterial Infections ◽  
Thiophene Ring ◽  
Docking Studies ◽  
Biological Evaluation ◽  
In Silico Docking ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Therapeutic Activities ◽  
Substituted 1

Newer antibacterial agents are needed to combat the growing bacterial infections. Triazoles are one of the leading and most sought out nucleus amongst the heterocyclic rings in the drug world. 1, 2, 3-Triazoles are synthesized by Click Chemistry of alkynes with azides. A synergistic effect is observed when the triazoles are combined with other heterocycles. They also exhibit diversified therapeutic activities like anti-viral, anti-bacterial, anti-diabetic, anti-tubercular, anti-inflam-matory, antihypertensive etc which makes Triazoles an interesting molecule for the researchers to work on. In the current study, we combined 1,2, 3-triazoles with thiophene ring system to get synergistic antibacterial activity. Here, 12 derivatives of 4, 5-substituted-1, 2, 3-Triazoles were subjected to in silico docking studies on Biotin ligase protein (PDB ID: 3V7R). The compounds that showed the best results were synthesized. The newly synthesized derivatives were characterized by using IR, H1 NMR and Mass spectrum. All the synthesized derivatives were evaluated for antibacterial activity against Gram-negative bacteria (E. coli and P. aerugenosa) and gram-positive bacteria (B. subtilis and S. aureus). The compounds showed moderate to good activity, which was comparable to that of the standard Streptomycin drug.

Design, Synthesis, Docking and Biological Evaluation of Novel 4-hydroxy Coumarin Derivatives

2020 ◽  
Vol 16 ◽  
Author(s):  
N. Ramalakshmi ◽  
S.R. Chitra ◽  
P. Manimegalai ◽  
S. Arunkumar
Keyword(s):  
Antibacterial Activity ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Coli Strain ◽  
Coumarin Derivatives ◽  
In Vivo Evaluation ◽  
E Coli ◽  
Tract Infections ◽  
Multiple Drugs

Background: Hospital acquired (HA) infections are caused due to E. coliwhich is resistant to multiple drugs particularly to fluroquinolone class of drugs. Urinary tract infections (UTI) affects people in the community and in hospitals. 150 million people per annum are suffering from UTI worldwide. Methods: In this present study we designed 36 novel coumarin derivatives, also we predicted pharmacokinetic and toxicity parameters. Docking studies were also carriedand all the compounds were evaluated for antibacterial activity againstresistant quinolone E. coli strain ATCC 25922. It was interesting to note thatthe introduction of electron withdrawing group on the aromatic ringresulted in compounds with increased antibacterial activity which is observed in compound 6 (with4-nitro substitution), compound 23(chloro) and compound 30(chloro, nitro). Results: From the MIC results, was observed that compounds 6, 23 and 30 showed higher activity with 0.5µg/ml, 0. 12 µg/ml, 0.5 µg/mlrespectively. Docking studies were performed with the activesite of DNA gyrase (PDB ID: 4CKK ).The maximum binding energy was found to be -10.7Kcal/mol. Conclusion: From the study it was found that 3 compounds were potentially active against quinolone resistant E. coli strains. This study can be further extended for in vivo evaluation.

scholarly journals Synthesis and Biological Screening of 3-Aryl-5-[(4′-Difluoromethoxy)(3′-Hydroxy)Phenyl]-4,5-Dihydro Isoxazole

2015 ◽  
Vol 47 ◽  
pp. 133-138
Author(s):  
V.N. Bhadani ◽  
H.D. Purohit ◽  
Dipak M. Purohit
Keyword(s):  
Antibacterial Activity ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Biological Activities ◽  
Gram Negative Bacteria ◽  
Biological Screening ◽  
Gram Negative ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Therapeutic Activities

Isoxazoline derivatives shows various types of therapeutic activities like antimicrobial[1], anti-inflammatory[2], anticonvulsant[3], Hypoglycemic[4] etc. getting to synthesized in view of 3-Aryl-5-[(4′-difluoromethoxy)(3′-hydroxy)phenyl]-4,5-dihydro isoxazole (4a-4i) have been synthesized. All the newly synthesized compounds were screened for their antibacterial activity against S. aureus, M. luteus (Gram-positive bacteria), E. coli, S. thyphi (Gram-negative bacteria) and antifungal activity against Candida albicans (Fungi). The biological activities (MIC) of the synthesized compounds were compared with known standard drugs.

PHYTOCHEMICAL AND ANTIBACTERIAL EVALUATION OF TEPHROSIA PURPUREA AND ITS ACTIVE CONSTITUENT GALLIC ACID

2017 ◽  
Vol 23 (1) ◽  
Author(s):  
JAVID AHMAD MALIK ◽  
SATENDRA KUMAR NIRALA ◽  
MONIKA BHADAURIA
Keyword(s):  
Antibacterial Activity ◽  
Gallic Acid ◽  
Bacterial Infections ◽  
Qualitative Evaluation ◽  
Antibacterial Activities ◽  
Bioactive Constituents ◽  
Active Constituent ◽  
E Coli ◽  
Tephrosia Purpurea ◽  
Therapeutic Activities

India is one of the hottest spot in the world in terms of biodiversity, but little is known about the chemical and pharmacological properties of most of the plants which needs to be explored. Tephrosia purpurea is one amongst the vital medicinal alternatives.In the present investigation, an attempt has been made to validate phytochemical composition of Tephrosia extract.Gallic acid is a good antioxidant and has been reported to possess various therapeutic activities. Thus, Tephrosia extract and gallic acid were screened against Staphylococcus aureus(gram +ve)and E. coli (gram -ve) for their antibacterial activities. Presence of different bioactive compounds were confirmed in Tephrosia extract by qualitative evaluation. Both Tephrosia extract and gallic acid possess strong antibacterial activity against gram +ve and gram –ve bacteria. Due to presence of several bioactive constituents and antibacterial activity, plant extract and gallic acid may be used as a therapeutic agent against a variety of diseases caused by bacterial infections.

Synthesis of Chalcones and Nucleosides Incorporating [1, 3, 4]Oxadiazolenone Core and Evaluation of their Antifungal and Antibacterial Activities

2020 ◽  
Vol 15 (6) ◽  
pp. 665-679
Author(s):  
Alok K. Srivastava ◽  
Lokesh K. Pandey
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Bacillus Subtilis ◽  
Antifungal Activity ◽  
Aspergillus Niger ◽  
Gram Negative ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Good Antibacterial Activity

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.

scholarly journals A novel bis(pyrazolyl)methane compound as a potential agent against Gram-positive bacteria

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Pedro Seguí ◽  
John J. Aguilera-Correa ◽  
Elena Domínguez-Jurado ◽  
Christian M. Sánchez-López ◽  
Ramón Pérez-Tanoira ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Inhibitory Effect ◽  
Eukaryotic Cell ◽  
Liver Carcinoma ◽  
Gram Positive ◽  
Minimal Inhibitory Concentrations ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Therapeutic Compounds ◽  
Toxic Concentrations

AbstractThis study was designed to propose alternative therapeutic compounds to fight against bacterial pathogens. Thus, a library of nitrogen-based compounds bis(triazolyl)methane (1T–7T) and bis(pyrazolyl)methane (1P–11P) was synthesised following previously reported methodologies and their antibacterial activity was tested using the collection strains of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Moreover, the novel compound 2P was fully characterized by IR, UV–Vis and NMR spectroscopy. To evaluate antibacterial activity, minimal inhibitory concentrations (MICs), minimal bactericidal concentrations (MBCs), minimum biofilm inhibitory concentrations (MBICs), and minimum biofilm eradication concentrations (MBECs) assays were carried out at different concentrations (2–2000 µg/mL). The MTT assay and Resazurin viability assays were performed in both human liver carcinoma HepG2 and human colorectal adenocarcinoma Caco-2 cell lines at 48 h. Of all the synthesised compounds, 2P had an inhibitory effect on Gram-positive strains, especially against S. aureus. The MIC and MBC of 2P were 62.5 and 2000 µg/mL against S. aureus, and 250 and 2000 µg/mL against E. faecalis, respectively. However, these values were > 2000 µg/mL against E. coli and P. aeruginosa. In addition, the MBICs and MBECs of 2P against S. aureus were 125 and > 2000 µg/mL, respectively, whereas these values were > 2000 µg/mL against E. faecalis, E. coli, and P. aeruginosa. On the other hand, concentrations up to 250 µg/mL of 2P were non-toxic doses for eukaryotic cell cultures. Thus, according to the obtained results, the 2P nitrogen-based compound showed a promising anti-Gram-positive effect (especially against S. aureus) both on planktonic state and biofilm, at non-toxic concentrations.

Preparation of bioactive and antibacterial PMMA-based bone cement by modification with quaternary ammonium and alkoxysilane

2021 ◽  
pp. 088532822110044
Author(s):  
Haiyang Wang ◽  
Toshinari Maeda ◽  
Toshiki Miyazaki
Keyword(s):  
Antibacterial Activity ◽  
Methyl Methacrylate ◽  
Bone Cement ◽  
Setting Time ◽  
Antibacterial Properties ◽  
The Body ◽  
Apatite Formation ◽  
Gram Positive ◽  
E Coli ◽  
Gram Positive Bacteria

Bone cement based on poly(methyl methacrylate) (PMMA) powder and methyl methacrylate (MMA) liquid is a very popular biomaterial used for the fixation of artificial joints. However, there is a risk of this cement loosening from bone because of a lack of bone-bonding bioactivity. Apatite formation in the body environment is a prerequisite for cement bioactivity. Additionally, suppression of infection during implantation is required for bone cements to be successfully introduced into the human body. In this study, we modified PMMA cement with γ-methacryloxypropyltrimetoxysilane and calcium acetate to introduce bioactive properties and 2-( tert-butylamino)ethyl methacrylate (TBAEMA) to provide antibacterial properties. The long-term antibacterial activity is attributed to the copolymerization of TBAEMA and MMA. As the TBAEMA content increased, the setting time increased and the compressive strength decreased. After soaking in simulated body fluid, an apatite layer was detected within 7 days, irrespective of the TBAEMA content. The cement showed better antibacterial activity against Gram-negative E. Coli than Gram-positive bacteria; however, of the Gram-positive bacteria investigated, B. subtilis was more susceptible than S. aureus.

scholarly journals Synthesis, Biological Evaluation and Docking Studies of 1,2,4,5-Tetrasubstituted Imidazoles as Antibacterial Agents: Use of Niobia Supported Heteropoly Tungstate as an Efficient Reusable Catalyst

2021 ◽  
Vol 33 (10) ◽  
pp. 2423-2429
Author(s):  
Aravind Kurnool ◽  
Karunasree Merugu ◽  
Pachipulusu Shravya ◽  
P. Malleswarareddy
Keyword(s):  
Antibacterial Activity ◽  
Catalytic Activity ◽  
Antibacterial Agents ◽  
Ammonium Acetate ◽  
Reaction Times ◽  
Binding Mode ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Reusable Catalyst ◽  
Tetrasubstituted Imidazoles

The synthesis of novel 1,2,4,5-tetrasubstituted imidazoles was carried out in a single molecular motif using niobia supported heteropoly tungstate as a mild and efficient reusable catalyst. The condensation of 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde, aromatic amine, benzil, ammonium acetate and heteropoly tungstate supported on niobia was achieved under both conventional and non-conventional conditions. The employed protocol provides significant advantages, as it exhibits a remarkable catalytic activity on recovery, excellent yields and excellent reaction efficacy within short reaction times between 1-2 h (conventional) and 1-3 min (microwave radiation). All the obtained compounds were characterized by means of spectral data and elemental analysis. They were also screened for their antibacterial activity. To predict the binding mode of compounds with glutamine-fructose-6-phosphate transaminase (GlcN6P synthase), docking studies were performed.

scholarly journals 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

2020 ◽  
Vol 13 (9) ◽  
pp. 229
Author(s):  
Volodymyr Horishny ◽  
Victor Kartsev ◽  
Vasyl Matiychuk ◽  
Athina Geronikaki ◽  
Petrou Anthi ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Minimal Bactericidal Concentration ◽  
Active Compounds ◽  
Hek 293 ◽  
E Coli ◽  
Thiazolyl Blue Tetrazolium Bromide

Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was S. aureus (American Type Culture Collection ATCC 6538), while L. monocytogenes (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound 5d (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9–113.8 μM, and Minimal bactericidal concentration MBC at 57.8–118.3 μM). Three most active compounds 5d, 5g, and 5k being evaluated against three resistant strains, Methicillin resistant Staphilococcus aureus (MRSA), P. aeruginosa, and E. coli, were more potent against MRSA than ampicillin (MIC at 248–372 μM, MBC at 372–1240 μM). At the same time, streptomycin (MIC at 43–172 μM, MBC at 86–344 μM) did not show bactericidal activity at all. The compound 5d was also more active than ampicillin towards resistant P. aeruginosa strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480–640 μM, and MFC at 640–800 μM) and ketoconazole (MIC 285–475 μM and MFC 380–950 μM). The best activity was exhibited by compound 5g. The most sensitive fungal was T. viride (IAM 5061), while A. fumigatus (human isolate) was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds 5d, 5g, 5k, 7c using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of E. coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.

Synthesis and photophysical, electrochemical, antibacterial, and DNA binding studies of triazinocalix[2]arenes

2015 ◽  
Vol 3 (16) ◽  
pp. 3340-3350 ◽  
Author(s):  
Kannan Rajavelu ◽  
Perumal Rajakumar
Keyword(s):  
Antibacterial Activity ◽  
Dna Binding ◽  
Docking Studies ◽  
Binding Studies ◽  
E Coli ◽  
Triazine Derivatives ◽  
Dna Binding Studies

The synthesized calix[2]arene[2]triazine derivatives bind effectively to DNA and exhibit efficient antibacterial activity against B. cereus, S. aureus and E. coli bacteria as supported by docking studies.

scholarly journals Water-dispersible glycosylated poly(2,5′-thienylene)porphyrin-based nanoparticles for antibacterial photodynamic therapy

2019 ◽  
Vol 18 (5) ◽  
pp. 1147-1155 ◽  
Author(s):  
Rehan Khan ◽  
Melis Özkan ◽  
Aisan Khaligh ◽  
Dönüs Tuncel
Keyword(s):  
Antibacterial Activity ◽  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Gram Negative Bacteria ◽  
Gram Positive ◽  
Gram Negative ◽  
E Coli ◽  
Water Dispersible ◽  
Gram Positive Bacteria ◽  
High Yields

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.

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