Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 3-10
Author(s):  
Aniket P. Sarkate ◽  
Kshipra S. Karnik ◽  
Pravin S. Wakte ◽  
Ajinkya P. Sarkate ◽  
Ashwini V. Izankar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Triazole Derivatives ◽  
Sar Studies ◽  
Convenient Synthesis ◽  
Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

scholarly journals Manganese (II) and Cobalt (II) Acetylacetonates as Antimicrobial Agents

2019 ◽  
Vol 1 ◽  
pp. 176-185
Author(s):  
S G Yiase ◽  
S O Adejo ◽  
S T Iningev
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Inhibitory Concentration ◽  
Dilution Method ◽  
Spectroscopic Techniques ◽  
Metal Chlorides ◽  
Activity Screening ◽  
Antibacterial And Antifungal ◽  
Broth Dilution

Mn(II) and Co(II) complexes were prepared by reaction of the metal chlorides with acetylacetone in ammonical aqueous medium. The metal complexes were prepared in order to investigate their antimicrobial activity on some selected pathogens. The characterisation of the complexes was on the basis of various spectroscopic techniques like infrared and ultraviolet studies. The compounds were subjected to antimicrobial activity screening using serial broth dilution method. Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal/Fungicidal Concentration (MBC/MFC) were determined. Mn(II) complex has shown significantly both antibacterial and antifungal activity with a MIC of 1.25 μg/mL while Co(II) complex was noticeable for antifungal activity at the same concentration. Whereas Mn(II) acetylacetonate is a more potent bactericide while Co(II) acetylacetonate is a more potent fungicide, both with MBC/MFC value of 2.5 μg/mL. Antimicrobial agent of the ligand has enhanced on complexation with Mn(II) and Co(II) ions. Though, the potency of the prepared antibiotics on the tested microbes is less compared to the standard drugs (Ciprofloxacin and Fulcin).

scholarly journals Synthesis, Molecular Docking and Evaluation of Library of 3-Mercapto-1,2,4-Triazole Derivatives as Antimicrobial Agents

2021 ◽  
Vol 33 (12) ◽  
pp. 3039-3046
Author(s):  
Swarnagowri Nayak ◽  
Santosh L. Gaonkar ◽  
Sushruta S. Hakkimane ◽  
Swapna B ◽  
Nitinkumar S. Shetty
Keyword(s):  
Antimicrobial Activity ◽  
Molecular Docking ◽  
In Silico ◽  
Structural Modification ◽  
Antimicrobial Agents ◽  
Antifungal Drugs ◽  
Aromatic Acids ◽  
Triazole Derivatives ◽  
In Silico Study ◽  
Antibacterial And Antifungal

Due to the increasing microbial resistance to antibacterial and antifungal drugs, the development of new antimicrobial agents is an urgent priority. In search of newer antimicrobial agents, a series of 4,5-disubstituted-3-mercapto-1,2,4-triazole derivatives were synthesized from aromatic acids and substituted isothiocyanates. The in silico study was performed to study the binding interactions of the synthesized compounds with the active pocket of CYP51. Among the synthesized 3-mercapto-triazole derivatives, compounds 6r, 6s and 6u exhibited promising antimicrobial activity comparable to standard drugs. The results suggested that the structural modification to 3-mercapto-1,2,4-triazole derivatives could lead to promising antimicrobial scaffolds.

scholarly journals Synthesis, antibacterial and antifungal activity of 1-[4-(1,1,3,3-tetramethylbutyl)phenoxy]-3-dialkylamino-2-propanol quaternary salts

2019 ◽  
pp. 56-62 ◽  
Author(s):  
Y. V. Korotkii ◽  
N. A. Vrynchanu ◽  
M. L. Dronova ◽  
Z. S. Suvorova ◽  
O. A. Smertenko
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Dilution Method ◽  
The Novel ◽  
Antibacterial And Antifungal Activity ◽  
Antimicrobial Drugs ◽  
Quaternary Salts ◽  
Resistant Strains ◽  
Antibacterial And Antifungal

The emergence and spread of resistant strains of pathogens as well as reduction of the efficacy of current antimicrobial agents requires the development of novel antimicrobial compounds. The aim of the present study was synthesis and evaluation of antimicrobial activity of new arylaliphatic aminopropanols. The objects of the present study were 1-[4-(1,1,3,3-tetramethylbutyl)phenoxy]-3-dialkylamino-2-propanol quaternary salts (compounds I–XIV). Compounds synthesis was carried out by heating of precursor epoxide and excessive amount of appropriate amines in isopropanole, followed by treatment with excess of alkyl halides. Methods of elemental analysis, IR- and PMR-spectroscopy were used for confirmation of chemical structure. Antimicrobial activity against Staphylococcus аureus АTCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa АТСС 27853 and Candida albicans NCTC 885/653 was determined by a broth dilution method and evaluated via minimum inhibitory concentration (MIC). Our investigation of antibacterial and antifungal activity of 1-[4-(1,1,3,3-tetra methylbutyl)phenoxy]-3-dialkylamino-2-propanol quaternary salts showed that compounds possess narrow spectrum, as well as broad spectrum action. Significant antimicrobial activity of the novel aryl aliphatic aminoalcohols indicates their potential usage as a component of new antimicrobial drugs.

scholarly journals EVALUATION OF POTENTIAL ANTIMICROBIAL ACTIVITY OF SYNTHETIC FLAVONOIDS

2021 ◽  
Vol 10 (1) ◽  
pp. 76-82
Author(s):  
Prabhulingayya S Bhixavatimath ◽  
Yasmeen Maniyar ◽  
Akram Naikawadi ◽  
Vijayakumar D
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Oxidative Cyclization ◽  
In Vivo Studies ◽  
Diffusion Method ◽  
Flavonoid Compounds ◽  
Antibacterial And Antifungal

Introduction: In recent times, most of the currently available antimicrobial agents have developed resistance. Extensive pharmacological activities including bactericidal and bacteriostatic nature of flavonoids, made them as priority agents in this aspect of research study. Synthetic flavonoids such as hydroxy thiophen derivatives were considered to evaluate for antimicrobial activity in this study.   Objective: The present study involves the analysis for antimicrobial activity of thiophen substituted synthetic flavonoids. Methods: Claisen-Schmidt method of condensation fallowed by oxidative cyclization reactions from substituted hydroxyacetophenone with aromatic aldehydes were used to synthesize the various analogues of flavonoid compounds. Then these compounds after their FTIR, 1H NMR, MS spectral characterization and elemental analysis, were screened for in vitro antibacterial and antifungal activity by using disc diffusion method followed by determining their respective zone of inhibitions. Results: All the synthesized test flavonoid compounds exhibited the good antibacterial and antifungal  spectrum activity over B. subtilis, S. aureus, E. coli and P. aeurugenosa bacteria and Candida albicans and Aspergillus niger fungal microbes. However compounds such as F1, F2 and F4 showed moderately significant antibacterial activity against P. aerugenosa organism than the other test compounds and the same F1 and F2 test compounds exhibited significant antifungal activity at100µg concentration. Conclusion:  The present study demonstrated that the novel thiophen substituted flavonoids (F1, F2, F3 and F4 ) found to have promising antimicrobial and antifungal activity which needs to be confirmed by in vivo studies.

scholarly journals Synthesis and antimicrobial evaluation of some novel thiomorpholine derived 1,4-disubstituted 1,2,3-triazoles

2016 ◽  
Vol 81 (3) ◽  
pp. 233-242 ◽  
Author(s):  
Kumaraswamy Battula ◽  
Sirassu Narsimha ◽  
Vasudevareddy Nagavelli ◽  
Priyanka Bollepelli ◽  
Rao Srinivasa
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Sodium Azide ◽  
Alkyl Halides ◽  
One Pot ◽  
Standard Drug ◽  
Convenient Synthesis ◽  
Antimicrobial Evaluation

A convenient synthesis of novel1,4-disubstituted 1,2,3-triazoles (4a-j & 5a-j) is reported via copper (I) - catalyzed one pot [3+2] cycloaddition of various alkyl halides, sodium azide with (prop-2-yn-1-yl)thiomorpholine and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide. All the synthesized compounds were investigated for their antimicrobial activity. Compounds 4a, 4b, 4c, 4g, 5a and 5j against S.epidermidis, 4a, 5a and 5d against P. aeroginosa, 4a, 4b and 4g against K.pneumoniae, 4b, 5a and 5d against S.aureus and 5b, 5e and 5j against B.Subtilis have shown excellent antibacterial activity compared to the standard drugs Penicillin and Streptomycin. Compounds 4c, 4e, 4f, 4j, 5c, 5d, 5g and 5j have registered moderate antifungal activity as compared with standard drug Ampothericin-B.

Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole- 3-1,1-dioxide Derivatives with Antimicrobial Activity and Docking Assisted Prediction of the Mechanism of their Antibacterial and Antifungal Properties

2020 ◽  
Vol 20 (29) ◽  
pp. 2681-2691
Author(s):  
Athina Geronikaki ◽  
Victor Kartsev ◽  
Phaedra Eleftheriou ◽  
Anthi Petrou ◽  
Jasmina Glamočlija ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Drug Targets ◽  
Bacterial Species ◽  
Pharmaceutical Research ◽  
Docking Studies ◽  
Fungal Species ◽  
Docking Analysis ◽  
E Coli ◽  
Antibacterial And Antifungal

Background: Although a great number of the targets of antimicrobial therapy have been achieved, it remains among the first fields of pharmaceutical research, mainly because of the development of resistant strains. Docking analysis may be an important tool in the research for the development of more effective agents against specific drug targets or multi-target agents 1-3. Methods: In the present study, based on docking analysis, ten tetrahydrothiazolo[2,3-a]isoindole derivatives were chosen for the evaluation of the antimicrobial activity. Results: All compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species being, in some cases, more potent than ampicillin and streptomycin against all species. The most sensitive bacteria appeared to be S. aureus and En. Cloacae, while M. flavus, E. coli and P. aeruginosa were the most resistant ones. The compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited good antifungal activity better than reference drugs bifonazole (1.4 – 41 folds) and ketoconazole (1.1 – 406 folds) against all fungal species. In order to elucidate the mechanism of action, docking studies on different antimicrobial targets were performed. Conclusion: According to docking analysis, the antifungal activity can be explained by the inhibition of the CYP51 enzyme for most compounds with a better correlation of the results obtained for the P.v.c. strain (linear regression between estimated binding Energy and log(1/MIC) with R 2 =0.867 and p=0.000091 or R 2 = 0.924, p= 0.000036, when compound 3 is excluded.

Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot

2014 ◽  
Vol 16 (9) ◽  
pp. 466-477 ◽  
Author(s):  
Ram Awatar Maurya ◽  
Praveen Reddy Adiyala ◽  
D. Chandrasekhar ◽  
Chada Narsimha Reddy ◽  
Jeevak Sopanrao Kapure ◽  
...  
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Rapid Access

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.

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