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.

scholarly journals Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies

Antibiotics ◽  
2020 ◽  
Vol 9 (5) ◽  
pp. 224 ◽  
Author(s):  
Lela Amiranashvili ◽  
Nanuli Nadaraia ◽  
Maia Merlani ◽  
Charalampos Kamoutsis ◽  
Anthi Petrou ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
In Silico ◽  
Web Applications ◽  
Experimental Studies ◽  
Docking Studies ◽  
Minimum Fungicidal Concentration ◽  
Antibacterial And Antifungal ◽  
Mic Minimum Inhibitory Concentration ◽  
Androstane Derivatives

We evaluated the antimicrobial activity of thirty-one nitrogen-containing 5-α-androstane derivatives in silico using computer program PASS (Prediction of Activity Spectra for Substances) and freely available PASS-based web applications (such as Way2Drug). Antibacterial activity was predicted for 27 out of 31 molecules; antifungal activity was predicted for 25 out of 31 compounds. The results of experiments, which we conducted to study the antimicrobial activity, are in agreement with the predictions. All compounds were found to be active with MIC (Minimum Inhibitory Concentration) and MBC (Minimum Bactericidal Concentration) values in the range of 0.0005–0.6 mg/mL. The activity of all studied 5-α-androstane derivatives exceeded or was equal to those of Streptomycin and, except for the 3β-hydroxy-17α-aza-d-homo-5α-androstane-17-one, all molecules were more active than Ampicillin. Activity against the resistant strains of E. coli, P. aeruginosa, and methicillin-resistant Staphylococcus aureus was also shown in experiments. Antifungal activity was determined with MIC and MFC (Minimum Fungicidal Concentration) values varying from 0.007 to 0.6 mg/mL. Most of the compounds were found to be more potent than the reference drugs Bifonazole and Ketoconazole. According to the results of docking studies, the putative targets for antibacterial and antifungal activity are UDP-N-acetylenolpyruvoylglucosamine reductase and 14-α-demethylase, respectively. In silico assessments of the acute rodent toxicity and cytotoxicity obtained using GUSAR (General Unrestricted Structure-Activity Relationships) and CLC-Pred (Cell Line Cytotoxicity Predictor) web-services were low for the majority of compounds under study, which contributes to the chances for those compounds to advance in the development.

scholarly journals Synthesis and Antimicrobial Screening of Some Novel 2, 5-Disubstituted 1, 3, 4-oxadiazole Derivatives

2011 ◽  
Vol 8 (s1) ◽  
pp. S149-S154 ◽  
Author(s):  
P. Panneerselvam ◽  
G. Geete Ganesh
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antibacterial And Antifungal Activity ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
E Coli ◽  
H Nmr ◽  
Oxadiazole Derivatives ◽  
Antibacterial And Antifungal ◽  
New Compounds

The syntheses of series of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives are described. A total of twelve new compounds were synthesized and characterized by IR,1H-NMR and Mass spectral data. All newly synthesized compounds were screened for their antimicrobial activityi.e. antibacterial activity againstS. aureusandE. coliand antifungal activity against fungusA. nigar. CompoundsG5andG7exhibited significant both antibacterial and antifungal activity whileG2,G10andG3,G9showed antibacterial and antifungal activity respectively. These compounds were 2, 5-disubstituted 1, 3, 4-oxadiazole moiety at position two and five showed reasonable antibacterial and antifungal activity.

scholarly journals Synthesis and Antimicrobial Activity of Some Aldehyde Derivatives of 3-Acetylchromen-2-one

2010 ◽  
Vol 7 (s1) ◽  
pp. S400-S404 ◽  
Author(s):  
B. Lakshminarayanan ◽  
V. Rajamanickam ◽  
T. Subburaju ◽  
L. A. Pradeep Rajkumar ◽  
H. Revathi
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Spectral Data ◽  
Aromatic Aldehyde ◽  
E Coli ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal ◽  
Derivatives Of

Some new 3-(substituted)-chromen-2-one have been synthesized by condensation of 3-acetylchromen-2-one with various aromatic aldehyde in presence of ethanol and alkali. The synthesized compounds were identified by spectral data and screened for their antibacterial activity againstB. pumilis, B. substilisandE. coliand antifungal activity againstA. nigerandCandida albicans. Among the synthesized compounds, some compounds of aryl chromen, which are having electron releasing substituent such as methoxy and hydroxyl at various positions, showed moderate to considerable antibacterial and antifungal activities.

scholarly journals Antimicrobial activity of secondary metabolites isolated from Centaurea spruneri Boiss.& Heldr.

2011 ◽  
Vol 76 (1) ◽  
pp. 27-34 ◽  
Author(s):  
Ana Ciric ◽  
Anastasia Karioti ◽  
Jasmina Glamoclija ◽  
Marina Sokovic ◽  
Helen Skaltsa
Keyword(s):  
Antimicrobial Activity ◽  
Protocatechuic Acid ◽  
Bacterial Species ◽  
Fungal Species ◽  
Antibacterial And Antifungal Activities ◽  
Fungistatic Activity ◽  
Microdilution Method ◽  
Aerial Parts ◽  
Antibacterial And Antifungal

Two coumarins, scopoletin (1) and isoscopoletin (2), two simple phenolic acids, protocatechuic acid (3) and isovanillic acid (4) and one flavonoid, eriodictyol (5) were isolated from the aerial parts of Centaurea spruneri. The structure of the compounds was established by spectroscopic methods. The in vitro antimicrobial activity of the isolated compounds was tested against eight bacteria and eight fungal species, using a microdilution method. All compounds tested showed moderate antibacterial and antifungal activities. Their minimum inhibitory concentrations were in the range 0.655 - 2.38 ?mol ml-1 and their minimal bactericidal concentrations ranged from 0.694 to 4.15 ?mol ml-1 against the tested bacterial species. All compounds showed fungistatic activity at 0.259 - 2.38 ?mol ml-1 and fungicidal at 0.69 - 2.6 ?mol ml-1 against all fungi tested.

scholarly journals Antibacterial and Antifungal Activity of Plant Extracts from Spinacia oleraceae L. (Amaranthaceae)

2021 ◽  
pp. 94-100
Author(s):  
Firza Shafique ◽  
Uzma Naureen ◽  
Annam Zikrea ◽  
Sohail Akhter ◽  
Tanzila Rafique ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Bacterial Species ◽  
Ethanolic Extract ◽  
Fungal Species ◽  
Diffusion Method ◽  
Root Extract ◽  
Antibacterial And Antifungal Activity ◽  
Zone Of Inhibition ◽  
Good Efficiency ◽  
Antibacterial And Antifungal

Spinach (Spinacia oleracea L. SO) leaves represent an important dietary source, have high nutritional value and antimicrobial properties. Spinach leaves have been used in the treatment of human diseases since ancient times. Here, the aim of this study was to evaluate the antimicrobial and antifungal activities of ethanolic extract of Spinach oleracea leaves by determining the minimum inhibitory concentrations (MICs) using well diffusion method against bacterial        species Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa and Staphylococcus aureus and Klebseilla pneumonia and fungal species Aspergillus fumigatus, Aspergillus niger,        Candida albicans and Fusarium oxysporum. We evaluated from present data that ethanolic extract of root showed zone of inhibition ranges from 6 mm to 21 mm, ethanolic extract of stem showed zone of inhibition ranges from 8 mm to 21 mm and ethanolic extract of leaf showed zone of inhibition ranges from 9 mm to 22 mm from concentration 25 mg/ml to 100mg/ml. Leaf extract has high antibacterial and antifungal activity against bacterial and fungal species while root extract has low antibacterial and antifungal activity against bacterial and fungal species. Activity of plant extract was increased by the increasing concentration of extracts. Very low zone of inhibition was found at concentration 25 mg/1 ml DMSO which ranges from 6 mm to 14 mm while very high zone of inhibition was found at concentration 100 mg/ml which ranges from 6 mm to 22 mm. So, ethanolic extracts of Spinach oleraceae has good efficiency against bacterial and fungal species.

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 Antibacterial and Antifungal Activity of Clove Extract (Syzygium Aromaticum): Review

2021 ◽  
Vol 2 (2) ◽  
pp. 93-103
Author(s):  
Nathaniel Hiwandika ◽  
Susana Elya Sudrajat ◽  
Ika Rahayu
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Ethanolic Extract ◽  
Therapeutic Effects ◽  
Syzygium Aromaticum ◽  
Antibacterial And Antifungal Activity ◽  
E Coli ◽  
Clove Essential Oil ◽  
Clove Extract ◽  
Antibacterial And Antifungal

Cloves is one of the native Indonesian plants and is used in many aspects of life. Cloves are used in multiple industries and as detergents, soaps, perfumes, food seasonings, aromatherapy, etc. Cloves are mainly used for ingredients in kretek cigarettes in Indonesia. Various studies of cloves reported they have good pharmacological and therapeutic effects. The main compounds of clove extract are eugenol and β-caryophyllene, which are powerful antibacterial and antifungal agents. The clove ethanolic extract showed the activity to inhibit Gram positive and negative bacteria such as B. cereus, S. aureus, E. coli, P. aeruginosa, S. pneumoniae, S. aureus, S. epidermidis, A. hydrophila, K. pneumoniae, P. gingivalis, and P. mirabilis. Clove essential oil has shown the ability to inhibit the growth of V. inaequalis, C. albicans, C. glabrata, and C. tropicalis. Cloves extract can be used as an essential ingredient of various medicines. However, it requires further research and trials.

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.

Chemical traits and antimicrobial activity of endemic Teucrium arduini L. from Mt Biokovo (Croatia)

2012 ◽  
Vol 7 (5) ◽  
pp. 941-947 ◽  
Author(s):  
Dario Kremer ◽  
Ivna Müller ◽  
Valerija Dunkić ◽  
Dubravka Vitali ◽  
Edith Stabentheiner ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Essential Oils ◽  
Bacterial Species ◽  
Glandular Trichomes ◽  
Toxic Metal ◽  
Antimicrobial Activities ◽  
Fungal Species ◽  
High Concentration ◽  
Sesquiterpene Hydrocarbons ◽  
Chemical Traits

AbstractChemical composition of the essential oil (analysed by GC-FID and GC-MS), the content of macroelements and trace elements (analysed by ICP-AES), and antimicrobial activities were investigated in Teucrium arduini L. from Mt Biokovo (Croatia). Additionally, a study on the types and distribution of glandular trichomes which produce essential oils was investigated. The oil was characterized by a high concentration of sesquiterpene hydrocarbons (68.5%) of which β-caryophyllene (32.9%) and germacrene D (16.4%) being the major compounds. Among the macroelements, the content of calcium was the highest (9772 mg/kg), while the content of sodium was the smallest (117.74 mg/kg). Among the micronutrients, the most represented element was iron (72.07 mg/kg). The content of each investigated toxic metal (As, Hg, Pb, Cd and Cr) was below permissible levels. The essential oils showed antimicrobial activity against bacterial species tested, with MIC values ranging from 6.25 mg/mL to 37.50 mg/mL. Fungal species were susceptible with MIC values from 7.81 mg/mL and 25.00 mg/mL.

scholarly journals Dithiosulfinates and Sulfoxides with Antifungal Activity from Bulbs of Allium sativum L. var. Voghiera

2018 ◽  
Vol 13 (9) ◽  
pp. 1934578X1801300
Author(s):  
Bruna de Falco ◽  
Giuliano Bonanomi ◽  
Virginia Lanzotti
Keyword(s):  
Antimicrobial Activity ◽  
Nmr Spectroscopy ◽  
Antifungal Activity ◽  
Botrytis Cinerea ◽  
Trichoderma Harzianum ◽  
Structure Elucidation ◽  
Allium Sativum ◽  
Fungal Species ◽  
Phytochemical Analysis ◽  
Spectroscopic Analyses

A bioassay guided phytochemical analysis of the bulbs of Allium sativum L. var. Voghiera, typical of Voghiera, Ferrara (Italy), allowed the isolation of six new sulfur compounds with dithiosulfinates and sulfoxides functionalities. Structure elucidation of the isolated compounds was carried out by spectroscopic analyses, including NMR spectroscopy and MS spectrometry. Compounds showed significant antimicrobial activity towards two fungal species, the air-borne pathogen Botrytis cinerea and the beneficial fungus Trichoderma harzianum.

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