Oxazolone–1,2,3-Triazole Hybrids: Design, Synthesis and Antimicrobial Evaluation

2018 ◽  
Vol 18 (17) ◽  
pp. 1506-1513 ◽  
Author(s):  
Kashmiri Lal ◽  
Lokesh Kumar ◽  
Ashwani Kumar ◽  
Anil Kumar
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Properties ◽  
Dilution Method ◽  
Antimicrobial Drugs ◽  
Activity Data ◽  
Design Synthesis ◽  
Docking Simulations ◽  
Comparable Activity ◽  
Antimicrobial Evaluation

Background: Oxazolones and 1,2,3-triazoles are among the extensively studied heterocycles in medicinal chemistry. Both of these moieties are reported to possess a broad spectrum of biological activity including antimicrobial. Objective: The objective of the current work is to design, synthesize and antimicrobial evaluation of some new oxazolone-1,2,3-triazole hybrids. Methods: The designed oxazolone-1,2,3-triazole hybrids were synthesized using copper(I)-catalyzed azide-alkyne cycloaddition. The antimicrobial evaluation was carried out using serial dilution method. Results: Most of the synthesized hybrids showed significant antimicrobial properties. Some of the compounds were found to be possessing better or comparable activity to that of the standards used. The docking simulations results are also in agreement with the antimicrobial activity data. Conclusion: Sixteen new hybrids were synthesized and tested in vitro for their antimicrobial activity. Some of the tested compounds exhibited promising antimicrobial activity and could be utilized for the development of the lead compounds for new and more potent antimicrobial drugs.

scholarly journals Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1-c][1,2,4]triazolo[3,4-f][1,2,4]triazines

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1339 ◽  
Author(s):  
Islam H. El Azab ◽  
Nadia A.A. Elkanzi
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Positive Control ◽  
Design Synthesis ◽  
Aspergillus Brasiliensis ◽  
In Vitro Investigation ◽  
Bacillus Subtilis Atcc ◽  
Antimicrobial Evaluation

A series of 34 new pyrimido[2,1-c][1,2,4]triazine-3,4-diones were synthesized and fully characterized using IR, NMR, MS, and microanalytical analysis. In vitro investigation of 12 compounds of this series revealed promising antimicrobial activity of the conjugates 15a and 15f–j that were tagged with electron-withdrawing groups, with sensitivities ranging from 77% to as high as 100% of the positive control. The investigation of antimicrobial activity included Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6535, Pseudomonas aeruginosa ATCC 27853, and Escherichia coli ATCC 8739 (EC), and fungal strains Candida albicans ATCC 10231 and Aspergillus brasiliensis ATCC 16404.

scholarly journals Design, Synthesis and In Vitro Antimicrobial Activity of 6-(1H-Benzimidazol-2-yl)-3,5-dimethyl-4-oxo-2-thio-3,4-dihydrothieno[2,3-d]pyrimidines

2021 ◽  
Vol 89 (4) ◽  
pp. 49
Author(s):  
Sergiy V. Vlasov ◽  
Olena D. Vlasova ◽  
Hanna I. Severina ◽  
Konstantin Y. Krolenko ◽  
Oleksandr V. Borysov ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Carboxylic Acid ◽  
Bacterial Resistance ◽  
Rapid Development ◽  
Antimicrobial Properties ◽  
Docking Studies ◽  
Antibacterial Drug ◽  
Design Synthesis ◽  
Drug Candidates

The rapid development in bacterial resistance to many groups of known antibiotics forces the researchers to discover antibacterial drug candidates with previously unknown mechanisms of action, one of the most relevant being the inhibition of tRNA (Guanine37-N1)-methyltransferase (TrmD). The discovery of selective TrmD inhibitors in the series of carboxamide derivatives of thienopyrimidines became a background for further modification of the similar structures aimed at the development of promising antibacterial agents. As part of this research, we carried out the construction of heterocyclic hybrids bearing the moieties of thieno[2,3-d]pyrimidine and benzimidazole starting from 3,5-dimethyl-4-oxo-2-thioxo-1H-thieno[2,3-d]pyrimidine-6-carboxylic acid, which was used as the pivotal intermediate. The hybrid molecule of 6-(1H-benzimidazol-2-yl)-3,5-dimethyl-2-thioxo-1H-thieno[2,3-d]pyrimidin-4-one prepared via condensation of the carboxylic acid with ortho-phenylenediamine was further alkylated with aryl/hetaryl chloroacetamides and benzyl chloride to produce the series of S-alkyl derivatives. The results of molecular docking studies for the obtained series of S-alkyl benzimidazole-thienopyrimidines showed their high affinity to the TrmD isolated from the P. aeruginosa. The results of antimicrobial activity screening revealed the antimicrobial properties for all of the studied molecules against both Gram-positive and Gram-negative bacteria and the Candida albicans fungal strain. The highest antimicrobial activity was determined for 2-{[6-(1H-benzimidazol-2-yl)-3,5-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl]thio}-N-(4-isopropylphenyl)acetamide, which also had the highest affinity to the TrmD inhibitor’s binding site according to the docking studies results.

New Caffeic Acid Derivatives as Antimicrobial Agents: Design, Synthesis, Evaluation and Docking

2019 ◽  
Vol 19 (4) ◽  
pp. 292-304 ◽  
Author(s):  
Maia Merlani ◽  
Vakhtang Barbakadze ◽  
Lela Amiranashvili ◽  
Lali Gogilashvili ◽  
Vladimir Poroikov ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Caffeic Acid ◽  
Antimicrobial Agents ◽  
Biological Activities ◽  
Antimicrobial Properties ◽  
Synthesis Methods ◽  
Design Synthesis ◽  
Caffeic Acid Derivatives ◽  
Microdilution Method

Background: Phenolic acids (caffeic-, ferulic and p-coumaric acid) are widely distributed in the plant kingdom and exhibit broad spectrum of biological activities, including antimicrobial activity. Objective: The goal of this paper is the synthesis of some caffeic acid derivatives selected based on computer-aided predictions and evaluate their in vitro antimicrobial properties against Gram positive and Gram negative bacteria and also a series of fungi. Methods: In silico prediction of biological activity was used to identify the most promising structures for synthesis and biological testing, and the putative mechanisms of their antimicrobial action. The designed compounds were synthesized using classical organic synthesis methods. The antimicrobial activity was studied using microdilution method. Results: Twelve tested compounds have shown good antibacterial activity. Five out of twelve tested compounds appeared to be more active than the reference drugs ampicillin and streptomycin. Despite that all compounds exhibited good activity against all bacteria tested, the sensitivity of bacteria towards compounds in general was different. The evaluation of antifungal activity revealed that all compounds were more active than ketoconazole, while seven compounds (2, 3, 4, 5, 7, 8 and 12) appeared to be more active than bifonazole. Docking results indicate that gyrase inhibition is the putative mechanism of antibacterial action while the inhibition of 14α-demethylase may be responsible for antifungal action. Prediction of cytotoxicity by PROTOX showed that compounds are not toxic (LD50 1000-2000 mg/kg). Conclusion: Thirteen compounds, from which six are new ones, were synthesized, and twelve compounds were tested for antimicrobial activity. The studied compounds appeared to be promising potent and non-toxic antimicrobials, which could be considered as leads for new pharmaceutical agents.

scholarly journals DESIGN, SYNTHESIS, AND PHARMACOLOGICAL EVALUATION OF SOME NOVEL BIS-THIAZOLE DERIVATIVES

2018 ◽  
Vol 11 (4) ◽  
pp. 164 ◽  
Author(s):  
Ramesh M Borde ◽  
Satish B Jadhav ◽  
Rahul R Dhavse ◽  
Achut S Munde
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Properties ◽  
Hantzsch Reaction ◽  
Thiazole Derivatives ◽  
Design Synthesis ◽  
Structure Activity ◽  
Elemental Analyses ◽  
And Staphylococcus Aureus ◽  
Toxic Molecule

 Objective: A series of substituted 5,2-bis-thiazoles derivatives were synthesized by Hantzsch reaction and evaluated in vitro for antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Staphylococcus aureus. Methods: 2-(4-(benzyloxy)phenyl)-4-methylthiazole-5-carbothioamide were synthesized and allowed to react with various α-haloketones to give 5,2-bis-thiazoles, i.e., 2-(4-(benzyloxy)phenyl)-4-methyl-5-(4-substituted thiazol-2-yl)thiazole derivatives in excellent yield. The synthesized compounds were characterized by spectroscopic methods as well as elemental analyses. They were screened for their antimicrobial activity using the agar diffusion method.Result: Literature survey reveals that the synthesis of 2-(4-(benzyloxy)phenyl)-4-methyl-5-(4-substituted thiazol-2-yl)thiazole, i.e., (5,2-Bis-thiazoles) derivatives (10a-e) was not reported. The entire compound exhibited mild to moderate antimicrobial activity.Conclusion: The antimicrobial results revealed that the synthesized derivatives have significant antimicrobial properties, and further, structure– activity relationship studies may develop more potent and less toxic molecule.

scholarly journals Synthesis of modified pyridine and bipyridine substituted coumarins as potent antimicrobial agents

2015 ◽  
Vol 80 (6) ◽  
pp. 739-747 ◽  
Author(s):  
Hemali Lad ◽  
Rakesh Giri ◽  
Yogita Chovatiya ◽  
Dinkar Brahmbhatt
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antimicrobial Agents ◽  
Molecular Hybridization ◽  
Dilution Method ◽  
Gram Negative ◽  
Comparable Activity ◽  
Broth Dilution ◽  
Substituted Coumarins

In search for new antimicrobial agents a series of new modified pyridine and bipyridine substituted coumarins 5a-y was designed and synthesized by adopting molecular hybridization strategy. All the synthesized compounds were evaluated for their in vitro antimicrobial activity using broth dilution method against selected bacterial (Gram-positive and Gram-negative) and fungal strains. Compounds 5a, 5f, 5g, 5n, 5r, 5t, 5w, 5x and 5y demonstrated promising antibacterial activity while other derivatives showed comparable activity to standard drugs used as reference.

Synthesis and Antimicrobial Evaluation of Benzimidazolyl pyrimido [4,5-b]quinolinones

2020 ◽  
Vol 17 ◽  
Author(s):  
Gumpula Prasoona ◽  
Baireddy Kishore ◽  
Gavaji Brahmeshwari
Keyword(s):  
Antimicrobial Activity ◽  
Drug Targets ◽  
Stannous Chloride ◽  
Ethyl Cyanoacetate ◽  
Antimicrobial Drugs ◽  
Antimicrobial Studies ◽  
Antimicrobial Evaluation ◽  
Bacteria And Fungi

Background: As infectious diseases causing bacteria and fungi are developing resistance to existing antimicrobial drugs, it is necessary to search for new drug targets with different structures and mode of action. Hence, it is essential to screen for new antimicrobial drugs with good efficacy and less toxicity. Methods: The reaction of 2-amino benzimidazoles 1 with ethyl cyanoacetate 2 afforded N-(1H-benzo[d]imidazol-2-yl)-2- cyanoacetamides 3. Compounds 3 on Knoevenagel condensation with o-nitro benzaldehydes 4 produced (E)-N-(1Hbenzo[d]imidazol-2-yl)-2-cyano-3-(2-nitrophenol) acylamides 5. Compounds 5 were converted to 2-amino –N-(1Hbenzo[d]imidazol-2-yl) quinoline-3-carboxamides 6 on treatment with stannous chloride by reductive cyclization. The target compounds viz., 3-(1H-benzo[d]imidazol-2-yl)-2-methylpyrimido [4, 5-b] quinolin-4(3H)-ones 7 were obtained by N-acetylation followed by cyclodehydration of compounds 6 in situ by treatment with acetic anhydride. Results: 3-(1H-Benzo[d]imidazol-2-yl)-2-methylpyrimido [4, 5-b] quinolin-4(3H)-ones 7 have been synthesized from commercially available materials in excellent yields. The title compounds 7a-h are evaluated for in vitro antimicrobial activity. Compounds 7e, 7f and 7h have shown more antimicrobial activity than that of standard drugs. Conclusion: The structures of all the newly synthesized compounds 3, 5, 6 & 7 are confirmed on the basis of spectral data. Antimicrobial studies of compounds 7a-h have revealed that compounds 7e and 7f have more efficient activity when compared to the standard drugs.

scholarly journals An In Vitro Study on the Antimicrobial Properties of Essential Oil Modified Resin Composite against Oral Pathogens

Materials ◽  
2020 ◽  
Vol 13 (19) ◽  
pp. 4383
Author(s):  
Barbara Lapinska ◽  
Aleksandra Szram ◽  
Beata Zarzycka ◽  
Janina Grzegorczyk ◽  
Louis Hardan ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Resin Composite ◽  
Antimicrobial Properties ◽  
In Vitro Study ◽  
Diffusion Method ◽  
Oral Pathogens

Modifying the composition of dental restorative materials with antimicrobial agents might induce their antibacterial potential against cariogenic bacteria, e.g., S.mutans and L.acidophilus, as well as antifungal effect on C.albicans that are major oral pathogens. Essential oils (EOs) are widely known for antimicrobial activity and are successfully used in dental industry. The study aimed at evaluating antibacterial and antifungal activity of EOs and composite resin material (CR) modified with EO against oral pathogens. Ten EOs (i.e., anise, cinnamon, citronella, clove, geranium, lavender, limette, mint, rosemary thyme) were tested using agar diffusion method. Cinnamon and thyme EOs showed significantly highest antibacterial activity against S.mutans and L.acidophilus among all tested EOs. Anise and limette EOs showed no antibacterial activity against S.mutans. All tested EOs exhibited antifungal activity against C.albicans, whereas cinnamon EO showed significantly highest and limette EO significantly lowest activity. Next, 1, 2 or 5 µL of cinnamon EO was introduced into 2 g of CR and microbiologically tested. The modified CR showed higher antimicrobial activity in comparison to unmodified one. CR containing 2 µL of EO showed the best antimicrobial properties against S.mutans and C.albicans, while CR modified with 1 µL of EO showed the best antimicrobial properties against L.acidophilus.

scholarly journals In vitro evaluation of the antimicrobial activity of five root canal sealers

2004 ◽  
Vol 15 (1) ◽  
pp. 30-35 ◽  
Author(s):  
Brenda Paula Figueiredo de Almeida Gomes ◽  
José Assis Pedroso ◽  
Rogério Castilho Jacinto ◽  
Morgana Eli Vianna ◽  
Caio Cezar Randi Ferraz ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Properties ◽  
Contact Method ◽  
Streptococcus Sanguis ◽  
Actinomyces Naeslundii ◽  
Agar Diffusion Test ◽  
Significant Difference ◽  
Ah Plus ◽  
Endodontic Sealers

The aim of the present study was to analyze the antimicrobial properties of five endodontic sealers: Endo Fill, Endomethasone, Endomethasone N, Sealer 26 and AH-Plus, against the following microorganisms: Candida albicans, Staphylococcus aureus, Enterococcus faecalis, Streptococcus sanguis and Actinomyces naeslundii. The sealers were tested immediately, 24 h, 48 h and 7 days after manipulation.The direct contact method through the observation of the microbial growth in liquid medium and the agar diffusion test were used to evaluate the antimicrobial properties of the sealers. The results, in both methodologies used, showed that immediately after manipulation, Endo-Fill and Endomethasone demonstrated the highest antimicrobial activity, with no statistically significant difference between them. Sealer 26 demonstrated the lowest antimicrobial activity. At all other times after manipulation, there were no statistically significant differences among all the sealers tested. In conclusion, none of the sealers totally inhibited the growth of the microorganisms. Furthermore, the antimicrobial activity of each sealer decreased with time and was dependent upon the microbial susceptibility to them.

scholarly journals Evaluating the Antimicrobial Activity of Commercially Available Herbal Toothpastes on Microorganisms Associated with Diabetes Mellitus

2013 ◽  
Vol 14 (5) ◽  
pp. 924-929 ◽  
Author(s):  
Reena Kulshrestha ◽  
J Kranthi ◽  
P Krishna Rao ◽  
Feroz Jenner ◽  
V Abdul Jaleel ◽  
...  
Keyword(s):  
Diabetes Mellitus ◽  
Antimicrobial Activity ◽  
Dental Health ◽  
Antibacterial Properties ◽  
Antimicrobial Properties ◽  
Test Organism ◽  
Diffusion Method ◽  
Zone Of Inhibition ◽  
Disk Diffusion Method

ABSTRACT Aim The present study was conducted to evaluate the efficacy of commercially available herbal toothpastes against the different periodontopathogens. Materials and methods Six herbal toothpastes that were commonly commercially available were included in the study. Colgate herbal, Babool, Meswak, Neem active, Dabur red toothpastes were tested for the study whereas sterile normal saline was used as control. Antimicrobial efficacies of dentifrices were evaluated against Streptococcus mutans and Actinobacillus actinomycetemcomitans. The antimicrobial properties of dentifrices were tested by measuring the maximum zone of inhibition at 24 hours on the Mueller Hinton Agar media inoculated with microbial strain using disk diffusion method. Each dentifrice was tested at 100% concentration (full strength). Results The study showed that all dentifrices selected for the study were effective against the entire test organism but to varying degree. Neem active tooth paste gave a reading of 25.4 mm as the zone of inhibition which was highest amongst all of the test dentifrices. Colgate Herbal and Meswak dentifrices recorded a larger maximum zone of inhibition, measuring 23 and 22.6 mm respectively, compared to other toothpastes. All other dentifrices showed the zone of inhibition to be between 17 and 19 mm respectively. Conclusion The antibacterial properties of six dentifrices were studied in vitro and concluded that almost all of the dentifrices available commercially had antibacterial properties to some extent to benefit dental health or antiplaque action. How to cite this article Jenner F, Jaleel VA, Kulshrestha R, Maheswar G, Rao PK, Kranthi J. Evaluating the Antimicrobial Activity of Commercially Available Herbal Toothpastes on Microorganisms Associated with Diabetes Mellitus. J Contemp Dent Pract 2013;14(5):924-929.

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