A CuAAC Based Click Chemistry Approach for Synthesis of Quinoxaline-1,2,3-Triazole Hybrid Molecular Library and Its Antimicrobial Evaluation

2021 ◽  
Vol 6 (3) ◽  
pp. 235-242
Author(s):  
Bhoomi M. Makwana ◽  
Yogesh T. Naliapara
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Spectral Data ◽  
Broad Spectrum ◽  
Bacterial Species ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Hybrid Molecules ◽  
Antimicrobial Evaluation ◽  
Molecular Library

Copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) methodology to develop a library of 3-methyl quinoxaline-1,2,3-triazole hybrid molecules. The designed molecules were synthesized via efficient and purification free method. The structures of the achieved compounds were recognized based on their spectral data. The antimicrobial activity for the synthesized compounds was evaluated against four bacterial species and two fungal strains. Six compounds are broad spectrum molecule, which can inhibit the growth of both Gram-positive and Gram-negative bacteria. Two molecules show mainly antifungal activity. Compound 6e shows highest antibacterial as well as antifungal activity.

scholarly journals Novel 4-Thiazolidinone Derivatives as Anti-Infective Agents: Synthesis, Characterization, and Antimicrobial Evaluation

2016 ◽  
Vol 2016 ◽  
pp. 1-8 ◽  
Author(s):  
Amit Gupta ◽  
Rajendra Singh ◽  
Pankaj K. Sonar ◽  
Shailendra K. Saraf
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Pseudomonas Fluorescens ◽  
Broad Spectrum ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Spectral Techniques ◽  
Fungal Strains ◽  
Gram Positive Bacteria ◽  
Antimicrobial Evaluation

A series of new 4-thiazolidinone derivatives was synthesized, characterized by spectral techniques, and screened for antimicrobial activity. All the compounds were evaluated against five Gram-positive bacteria, two Gram-negative bacteria, and two fungi, at concentrations of 50, 100, 200, 400, 800, and 1600 µg/mL, respectively. Minimum inhibitory concentrations of all the compounds were also determined and were found to be in the range of 100–400 µg/mL. All the compounds showed moderate-to-good antimicrobial activity. Compounds4a[2-(4-fluoro-phenyl)-3-(4-methyl-5,6,7,8-tetrahydro-quinazolin-2-yl)-thiazolidin-4-one] and4e[3-(4,6-dimethyl-pyrimidin-2-yl)-2-(2-methoxy-phenyl)-thiazolidin-4-one] were the most potent compounds of the series, exhibiting marked antimicrobial activity againstPseudomonas fluorescens,Staphylococcus aureus,and the fungal strains. Thus, on the basis of results obtained, it may be concluded that synthesized compounds exhibit a broad spectrum of antimicrobial activity.

Synthesis and evaluation of chromene-based compounds containing pyrazole moiety as antimicrobial agents

2017 ◽  
Vol 23 (1) ◽  
Author(s):  
Mohamed Salah K. Youssef ◽  
Ahmed Abdou O. Abeed ◽  
Talaat I. El-Emary
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Spectral Data ◽  
Elemental Analysis ◽  
Antimicrobial Agents ◽  
Diffusion Method ◽  
Gram Negative Bacteria ◽  
Gram Positive ◽  
Gram Negative ◽  
Hybrid Compounds

AbstractWith an intention to synergize the antimicrobial activity of 1,3-diphenyl pyrazole and chromene derivatives, 20 hybrid compounds were synthesized and evaluated for their antimicrobial activity. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All compounds were evaluated for their antimicrobial activity against Gram positive and Gram negative bacteria and antifungal activity by a well diffusion method. Compounds

scholarly journals Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2793 ◽  
Author(s):  
Ameen Abu-Hashem
Keyword(s):  
Antimicrobial Activity ◽  
Growth Inhibition ◽  
Spectral Data ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Bacteria And Fungi ◽  
New Compounds

Substituted-6-methyl-1-thioxo-1,2-dihydro-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (5a,b) were synthesized from condensation of visnagenone (2a) or khellinone (2b) with 6-amino-thiouracil (3) in dimethylformamide or refluxing of (4a) or (4b) in dimethylformamide. Hence, compounds (5a,b) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (6a,b), furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazolinone (7a,b), substituted-benzylidene-furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (8a–f), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (9a,b), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (10a,b), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (11a–d), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (12a,b), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (13a,b) and 6-methyl-1-((piperazine) or morpholino)-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (14a–d). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, 1H-NMR, 13C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines 8a–f and 11a–d displayed results excellent for growth inhibition of bacteria and fungi.

scholarly journals Multidrug Pump Inhibitors Uncover Remarkable Activity of Plant Antimicrobials

2002 ◽  
Vol 46 (10) ◽  
pp. 3133-3141 ◽  
Author(s):  
George Tegos ◽  
Frank R. Stermitz ◽  
Olga Lomovskaya ◽  
Kim Lewis
Keyword(s):  
Broad Spectrum ◽  
Plant Pathogens ◽  
Bacterial Species ◽  
Permeability Barrier ◽  
Gram Negative Bacteria ◽  
Human Pathogens ◽  
Gram Negative ◽  
Low Level ◽  
Broad Spectrum Antibiotics ◽  
Level Of Activity

ABSTRACT Plant antimicrobials are not used as systemic antibiotics at present. The main reason for this is their low level of activity, especially against gram-negative bacteria. The reported MIC is often in the range of 100 to 1,000 μg/ml, orders of magnitude higher than those of common broad-spectrum antibiotics from bacteria or fungi. Major plant pathogens belong to the gram-negative bacteria, which makes the low level of activity of plant antimicrobials against this group of microorganisms puzzling. Gram-negative bacteria have an effective permeability barrier, comprised of the outer membrane, which restricts the penetration of amphipathic compounds, and multidrug resistance pumps (MDRs), which extrude toxins across this barrier. It is possible that the apparent ineffectiveness of plant antimicrobials is largely due to the permeability barrier. We tested this hypothesis in the present study by applying a combination of MDR mutants and MDR inhibitors. A panel of plant antimicrobials was tested by using a set of bacteria representing the main groups of plant pathogens. The human pathogens Pseudomonas aeruginosa, Escherichia coli, and Salmonella enterica serovar Typhimurium were also tested. The results show that the activities of the majority of plant antimicrobials were considerably greater against the gram-positive bacteria Staphylococcus aureus and Bacillus megaterium and that disabling of the MDRs in gram-negative species leads to a striking increase in antimicrobial activity. Thus, the activity of rhein, the principal antimicrobial from rhubarb, was potentiated 100- to 2,000-fold (depending on the bacterial species) by disabling the MDRs. Comparable potentiation of activity was observed with plumbagin, resveratrol, gossypol, coumestrol, and berberine. Direct measurement of the uptake of berberine, a model plant antimicrobial, confirmed that disabling of the MDRs strongly increases the level of penetration of berberine into the cells of gram-negative bacteria. These results suggest that plants might have developed means of delivering their antimicrobials into bacterial cells. These findings also suggest that plant antimicrobials might be developed into effective, broad-spectrum antibiotics in combination with inhibitors of MDRs.

scholarly journals Lipid Segregation Explains Selective Toxicity of a Series of Fragments Derived from the Human Cathelicidin LL-37

2009 ◽  
Vol 53 (9) ◽  
pp. 3705-3714 ◽  
Author(s):  
Raquel F. Epand ◽  
Guangshun Wang ◽  
Bob Berno ◽  
Richard M. Epand
Keyword(s):  
Antimicrobial Activity ◽  
Bacterial Species ◽  
Antimicrobial Activities ◽  
Gram Negative Bacteria ◽  
Selective Toxicity ◽  
Gram Positive ◽  
Gram Negative ◽  
Cytoplasmic Membranes ◽  
Anionic Lipids ◽  
Active Segment

ABSTRACT The only human cathelicidin, the 37-residue peptide LL-37, exhibits antimicrobial activity against both gram-positive and gram-negative bacteria. We studied the ability of several fragments of LL-37, exhibiting different antimicrobial activities, to interact with membranes whose compositions mimic the cytoplasmic membranes of gram-positive or of gram-negative bacteria. These fragments are as follows: KR-12, the smallest active segment of LL-37, with the sequence KRIVQRIKDFLR, which exhibits antimicrobial activity only against gram-negative bacteria; a slightly smaller peptide, RI-10, missing the two cationic residues at the N and C termini of KR-12, which has been shown not to have any antimicrobial activity; a longer peptide, GF-17, which shows antimicrobial activity against gram-positive as well as gram-negative bacteria; and GF-17D3, with 3 d-amino-acid residues, which is also selective only for gram-negative bacteria. Those fragments with the capacity to cluster anionic lipids away from zwitterionic lipids in a membrane exhibit selective toxicity toward bacteria containing zwitterionic as well as anionic lipids in their cytoplasmic membranes but not toward bacteria with only anionic lipids. This finding allows for the prediction of the bacterial-species selectivity of certain agents and paves the way for designing new antimicrobials targeted specifically toward gram-negative bacteria.

scholarly journals Syntheses, Characterization and Antimicrobial Evaluation of Some 1, 3, 5-Trisubustituted Pyrazole Derivatives

2010 ◽  
Vol 7 (4) ◽  
pp. 1190-1195 ◽  
Author(s):  
Vertika Gautam ◽  
Viney Chawla ◽  
Pankaj k. Sonar ◽  
Shailendra K. Saraf
Keyword(s):  
Antimicrobial Activity ◽  
Moderate Activity ◽  
Gram Negative Bacteria ◽  
Pyrazole Derivatives ◽  
Gram Positive ◽  
Gram Negative ◽  
E Coli ◽  
Antimicrobial Evaluation

A series of 1, 3, 5-trisubustituted pyrazole derivatives were synthesized and screened for antimicrobial activity. The compounds(2j-o)were evaluated against two gram-positive and two gram-negative bacteria and one fungus, at concentrations of 10 µg/mL and 50 µg/mL. The compounds were founds to be inactive againstP. aeruginosaandA. nigerbut exhibited moderate activity againstB. subtilis, E. coliandS. aureus. It can be concluded that the newly synthesized compounds possess promising antimicrobial activity.

scholarly journals Peptidomic Analysis of Skin Secretions of the Caribbean Frogs Leptodactylus insularum and Leptodactylus nesiotus (Leptodactylidae) Identifies an Ocellatin with Broad Spectrum Antimicrobial Activity

Antibiotics ◽  
2020 ◽  
Vol 9 (10) ◽  
pp. 718 ◽  
Author(s):  
Gervonne Barran ◽  
Jolanta Kolodziejek ◽  
Laurent Coquet ◽  
Jérôme Leprince ◽  
Thierry Jouenne ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Broad Spectrum ◽  
Antimicrobial Agents ◽  
Therapeutic Potential ◽  
Multidrug Resistant ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Peptidomic Analysis ◽  
Skin Secretions ◽  
Long Acting

Ocellatins are peptides produced in the skins of frogs belonging to the genus Leptodactylus that generally display weak antimicrobial activity against Gram-negative bacteria only. Peptidomic analysis of norepinephrine-stimulated skin secretions from Leptodactylus insularum Barbour 1906 and Leptodactylus nesiotus Heyer 1994, collected in the Icacos Peninsula, Trinidad, led to the purification and structural characterization of five ocellatin-related peptides from L. insularum (ocellatin-1I together with its (1–16) fragment, ocellatin-2I and its (1–16) fragment, and ocellatin-3I) and four ocellatins from L. nesiotus (ocellatin-1N, -2N, -3N, and -4N). While ocellatins-1I, -2I, and -1N showed a typically low antimicrobial potency against Gram-negative bacteria, ocellatin-3N (GIFDVLKNLAKGVITSLAS.NH2) was active against an antibiotic-resistant strain of Klebsiella pneumoniae and reference strains of Escherichia coli, K. pneumoniae, Pseudomonas aeruginosa, and Salmonella typhimurium (minimum inhibitory concentrations (MICs) in the range 31.25–62.5 μM), and was the only peptide active against Gram-positive Staphylococcus aureus (MIC = 31.25 μM) and Enterococcus faecium (MIC = 62.5 μM). The therapeutic potential of ocellatin-3N is limited by its moderate hemolytic activity (LC50 = 98 μM) against mouse erythrocytes. The peptide represents a template for the design of long-acting, non-toxic, and broad-spectrum antimicrobial agents for targeting multidrug-resistant pathogens.

Synthesis, antibacterial, and antifungal activities of new pyrimidinone derivatives

2015 ◽  
Vol 21 (4) ◽  
pp. 191-194 ◽  
Author(s):  
Oussama Cherif ◽  
Fatma Masmoudi ◽  
Fatma Allouche ◽  
Fakher Chabchoub ◽  
Mohamed Trigui
Keyword(s):  
Antimicrobial Activity ◽  
Broad Spectrum ◽  
Pathogenic Fungi ◽  
Gram Negative Bacteria ◽  
Efficient Synthesis ◽  
Gram Negative ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Bacteria And Fungi ◽  
Antibacterial And Antifungal

AbstractAn efficient synthesis of new pyrrolopyrimidinones 3a-d and isoxazolopyrimidinones 4a-c from the respective aminocyanopyrroles 1a-d and aminocyanoisoxazoles 2a-c is presented. The synthesized compounds were screened for antimicrobial activity against a panel of bacteria and fungi. Compound 4c exhibits remarkable activity against a broad spectrum of Gram-positive and Gram-negative bacteria and pathogenic fungi.

scholarly journals Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

Pharmaceutics ◽  
2019 ◽  
Vol 11 (6) ◽  
pp. 287 ◽  
Author(s):  
Diego Romano Perinelli ◽  
Dezemona Petrelli ◽  
Luca Agostino Vitali ◽  
Giulia Bonacucina ◽  
Marco Cespi ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Quaternary Ammonium ◽  
Cationic Surfactants ◽  
Cytotoxic Effect ◽  
Bacterial Species ◽  
Gram Negative Bacteria ◽  
Gram Positive ◽  
Gram Negative ◽  
Wide Range ◽  
Surface Active

Quaternary ammonium amphiphiles are a class of compounds with a wide range of commercial and industrial uses. In the pharmaceutical field, the most common quaternary ammonium surfactant is benzalkonium chloride (BAC), which is employed as a preservative in several topical formulations for ocular, skin, or nasal application. Despite the broad antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as fungi and small enveloped viruses, safety concerns regarding its irritant and cytotoxic effect on epithelial cells still remain. In this work, quaternary ammonium derivatives of leucine esters (C10, C12 and C14) were synthesised as BAC analogues. These cationic surfactants were characterised in terms of critical micelle concentration (CMC, by tensiometry), cytotoxicity (MTS and LDH assays on the Caco-2 and Calu-3 cell lines) and antimicrobial activity on the bacterial species Staphylococcus aureus and Enterococcus faecalis among the Gram-positives, Escherichia coli and Pseudomonas aeruginosa among the Gram-negatives and the yeast Candida albicans. They showed satisfactory surface-active properties, and a cytotoxic effect that was dependent on the length of the hydrophobic chain. Lower minimum inhibiting concentration (MIC) values were calculated for C14-derivatives, which were comparable to those calculated for BAC toward Gram-positive bacteria and slightly higher for Gram-negative bacteria and C. albicans. Thus, the synthesised leucine-based quaternary ammonium cationic surfactants can potentially find application as promising surface-active compounds with antimicrobial activity.

Sign in / Sign up

Export Citation Format

Share Document