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.

scholarly journals Invitro antibacterial activity of Cassia fistula Linn methanolic leaf extracts

2019 ◽  
Vol 8 (2) ◽  
pp. 270
Author(s):  
Bindhu R. Kamath ◽  
Sabeena Kizhedath
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Diffusion Method ◽  
Bacterial Strains ◽  
Cassia Fistula ◽  
Leaf Extracts ◽  
E Coli

Background: Cassia fistula Linn is a plant which is widely grown in India and is used for medicinal purposes. The study was carried out with an objective to demonstrate the antimicrobial activity of leaves of Cassia fistula Linn. The aim of the study is to assess antibacterial and antifungal activity of methanolic leaf extract of Cassia fistula Linn against selected clinical isolates.Methods: The antimicrobial activity of methanolic extract of Cassia fistula was evaluated using agar well diffusion method and to zone of inhibition of extract was determined. Clinical isolates of Staphyloccocus aureus, MRSA, Pseudomonas aeruginosa, E. coli and Proteus were screened.Results: The methanolic extracts exhibited antibacterial activity against Staphylococcus aureus. The extract was not active against E. coli, Proteus, MRSA, Pseudomonas aeruginosa. The extract also failed to demonstrate antifungal activity against Candida albicans and Aspergillus niger.Conclusions: The global emergence of multidrug resistant bacterial strains is increasing, limiting the effectiveness of current drugs and treatment failure of infections. A novel approach to the prevention of antibiotic resistance of pathogenic species is the use of new compounds that are not based on existing synthetic antimicrobial agents.

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF 3-FORMYL INDOLE BASED SCHIFF BASES

2018 ◽  
Vol 7 (6) ◽  
Author(s):  
Singh Gurvinder ◽  
Singh Prabhsimran ◽  
Dhawan R. K.
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Analysis ◽  
Schiff Bases ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Fungal Strain ◽  
Bacterial Strains ◽  
Standard Drug ◽  
Gram Negative ◽  
E Coli

In order to develop new antimicrobial agents, a series of 3-formyl indole based Schiff bases were synthesized by reacting 3-formyl indole(indole-3-carboxaldehyde) with substituted aniline taking ethanol as solvent. The reaction was carried in the presence of small amount of p-toluene sulphonic acid as catalyst.All the synthesized compounds were characterized by IR, 1H-NMR spectral analysis. All the synthesized compounds were evaluated for antimicrobial activity against two gram positive bacterial strains (B. subtilisand S. aureus) and two gram negative bacterial strains (P. aeruginosaand E. coli) and one fungal strain (C. albicans). All the synthesized compounds were found to have moderate to good antimicrobial activity. The  standard drug amoxicillin, fluconazole were used for antimicrobial activity. Among the synthesized compounds, the maximum antimicrobial activity was shown by compounds GS04, GS07, GS08 and GS10.

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 Synthesis of Phthalyl Substituted Imidazolones and Schiff Bases as Antimicrobial Agents

2011 ◽  
Vol 8 (1) ◽  
pp. 427-434
Author(s):  
Pramilla Sah ◽  
Neha Saraswat ◽  
Manu Manu
Keyword(s):  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Schiff Bases ◽  
Phthalic Anhydride ◽  
Thionyl Chloride ◽  
Antimicrobial Agents ◽  
Spectral Techniques ◽  
E Coli ◽  
H Nmr ◽  
Ethanoic Acid

A new series of phthalyl substituted imidazolones (4a–g) and Schiff bases (5a–d) were synthesized from 2-methyl-(m-nitro-1,3-dioxo-1,3-dihydro-(2H)-isoindole-2-yl)-5-amino-1,3,4-thiadiazole (3a–b). Compounds (3a–b) were prepared by cyclisation of 2-(m-nitro-1,3-dioxo-1,3-dihydro-(2H)-isoindole-2-yl)methyl ethanoate (2) with thiosemicarbazide. 2-(m-nitro-1,3-dioxo-1,3-dihydro-(2H)-isoindole-2-yl)ethanoic acid (1) in presence of thionyl chloride and methanol gave the ester (2) while compound (1) was synthesized by aminolysis of phthalic anhydride with glycine. The compounds were characterized by spectral techniques of IR,1H NMR, Mass and elemental analysis. All the synthesized compounds (4a–g) and (5a–d) were screened for their antibacterial activity against the pathogenic strainsE. coli, P. aureus, C. freundiiwhile antifungal activity was evaluated againstA. niger, A. flavus, Penicillium sp. and C. albicans.

scholarly journals Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4129 ◽  
Author(s):  
Joanna Kozłowska ◽  
Bartłomiej Potaniec ◽  
Dagmara Baczyńska ◽  
Barbara Żarowska ◽  
Mirosław Anioł
Keyword(s):  
Antimicrobial Activity ◽  
Cell Lines ◽  
Antimicrobial Agents ◽  
Human Colon ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Human Colon Cancer ◽  
E Coli ◽  
Almost All ◽  
Ht 29

A series of 18 aminochalcone derivatives were obtained in yields of 21.5–88.6% by applying the classical Claisen-Schmidt reaction. Compounds 4–9, 14 and 16–18 with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines—HT-29, LS180, LoVo and LoVo/DX —using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC50 value. The best results were observed for 2′-aminochalcone (1), 3′-aminochalcone (2) and 4′-aminochalcone (3) (IC50 = 1.43–1.98 µg·mL−1) against the HT-29 cell line and for amino-nitrochalcones 10–12 (IC50 = 2.77–3.42 µg·mL−1) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: Escherichia coli ATCC10536 and Staphylococcus aureus DSM799, the yeast strain Candida albicans DSM1386 and three strains of fungi: Alternaria alternata CBS1526, Fusarium linii KB-F1 and Aspergillus niger DSM1957. In the case of E. coli ATCC10536 almost all derivatives hindered the bacterial growth (∆OD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (3), that completely limited the growth of all tested strains at the concentration range of 0.25–0.5 mg·mL−1. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (14), that prevented the growth of E. coli ATCC10536 with MIC = 0.0625 mg·mL−1.

scholarly journals Synthesis and biological evaluation of some new 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines as antimicrobial agents

2022 ◽  
Vol 11 (1) ◽  
pp. 75-82 ◽  
Author(s):  
Iryna Myrko ◽  
Taras Chaban ◽  
Vasyl Matiychuk
Keyword(s):  
Mass Spectrometry ◽  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Pseudomonas Aeruginosa ◽  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Bacterial Strains ◽  
Synthesis And Biological Evaluation

A series of some new pyrazole-substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines was synthesized in this study. The structures of target substances were confirmed by using 1H and 13С NMR spectroscopy, mass spectrometry and elemental analysis. The synthesized compounds have been evaluated for antimicrobial activity against five bacterial strains (Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus) and two fungal strains (Candida albicans and Cryptococcus neoformans). The antimicrobial screening studies of synthesized substances established that 2 of 12 compounds show pronounced antibacterial activity against the strain Staphylococcus aureus.

Synthesis and Biological Evaluation of Chalconyl Incorporated Schiff’s Bases of Sulphonamides

2017 ◽  
Vol 8 (03) ◽  
Author(s):  
Neeraj Kumar ◽  
Dhruti Bhatt ◽  
Chandra Shekhar Sharma ◽  
Hamendra Pratap Singh ◽  
Harshda Pandiya ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Biological Evaluation ◽  
Antibacterial And Antifungal Activity ◽  
Schiff’S Bases ◽  
E Coli ◽  
Schiff's Bases ◽  
Microbial Strains ◽  
Antibacterial And Antifungal ◽  
Synthesis And Biological Evaluation

A series of of Chalconyl Incorporated Schiff’s Bases of Sulphonamides was synthesized by reacting substituted chalcone derivatives with Sulphacetamide sodium in methanol. All the title compounds synthesized (2a-2d) were tested for antibacterial and antifungal activity using E. coli, P. aeruginosa, S. aureus, S. pyogenus and C. albicans, A. niger and A. clavatus respectively as microbial strains and Sulphacetamide sodium as standard. The compound 2d showed significant antibacterial activity and 2a showed moderate antifungal activity as compared with Sulphacetamide Sodium.

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 Synthesis and Antimicrobial Activity of Metal-Containing Linseed Oil-Based Waterborne Urethane Oil Wood Coatings

Polymers ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 663 ◽  
Author(s):  
Kun-Tsung Lu ◽  
Jing-Ping Chang
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antimicrobial Agents ◽  
Linseed Oil ◽  
White Rot ◽  
White Rot Fungus ◽  
Manganese Acetate ◽  
Film Properties ◽  
E Coli ◽  
Significant Difference

In this study, the antimicrobial agents of mono(hydroxyethoxyethyl)phthalate (M(HEEP)2) with different metal of M = Zn, Mn, Pb, and Ca were synthesized from diethylene glycol (DEG), phthalic anhydride (PA), and divalent metal acetates including calcium acetate, zinc acetate, manganese acetate, and lead acetate, respectively. The waterborne urethane oil (WUO) dispersions synthesized from linseed oil, diisocyanates (hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI)), dimethylolpropionic acid at NCO/OH molars of 0.9, by acetone processing method were described as in our previous report. The M(HEEP)2 antimicrobial agents as well as the commercial nanosilver powder were added into WUO dispersions as the antimicrobial coatings. The effects of various antimicrobial agents and dosages (0.0, 0.2, 0.6, 0.8, 1.0, 2.0, and 4.0 phr) on antimicrobial activity of WUO films against gram-negative bacterium of Escherichia coli, gram-positive bacterium of Staphylococcus aureus, brown-rot fungus of Gloeophyllum trabeum, and white-rot fungus of Lenzites betulina were assessed. In addition, the film properties of the best antimicrobial WUO coatings were also examined. The results showed that the antimicrobial agents of mono(hydroxyethoxyethyl) phthalate M(HEEP)2 (M = Zn, Mn, Pb, and Ca) powders should certainly be synthesized by FTIR, 1H-NMR, 13C-NMR, and energy-dispersive X-ray spectroscopy (EDS) identifications and the yields of them were 43–55%. The results also revealed that the WUO film synthesizing with HDI films containing Zn(HEEP)2 of 2.0 phr and Pb(HEEP)2 of 0.4 phr had the best antibacterial activity for E. coli and S. aureus, respectively. The IPDI films containing Zn(HEEP)2 of 1.0 phr had the best antibacterial activity for both E. coli and S. aureus. For antifungal activity, the WUO film synthesizing with HDI films containing Pb(HEEP)2 of 0.8 phr and Zn(HEEP)2 of 2.0 phr as well as IPDI films containing Mn(HEEP)2 of 0.2 phr and Zn(HEEP)2 of 4.0 phr had the best performances against G. trabeum and L. betulina, respectively. Comparing with commercial nanoAg powder, the Zn(HEEP)2 and Pb(HEEP)2 had a superior antifungal efficiency for G. trabeum and L. betulina, while it had a slightly inferior efficiency in the antibacterial activity for E. coli and S. aureus. On the properties of WUO films, adding metal-containing antimicrobial agents could slightly enhance the thermal stability, but lowered the gloss of all films, however, the Tg value increased for HDI film and decreased for IPDI film. In addition to this, they had no significant difference in the film properties including hardness, impact resistance, bending resistance, adhesion, mass retention, and light-fastness between the WUO films with and without adding antimicrobial agents.

scholarly journals Facile Synthesis, Characterization, and In Vitro Antimicrobial Screening of a New Series of 2,4,6-Trisubstituted-s-triazine Based Compounds

2015 ◽  
Vol 2015 ◽  
pp. 1-10
Author(s):  
Ravi Bhushan Singh ◽  
Nirupam Das ◽  
Md. Kamaruz Zaman
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Elemental Analysis ◽  
Broad Spectrum ◽  
Antibacterial Efficacy ◽  
Facile Synthesis ◽  
Standard Drug ◽  
E Coli

A series of new 2,4,6-trisubstituted-s-triazine was synthesized, assessed for antimicrobial activity, and characterized by FTIR, 1HNMR, 13CNMR, and elemental analysis. The tested compounds, 4d, 4g, 4h, 4k, and 4n, have shown considerable in vitro antibacterial efficacy with reference to the standard drug ciprofloxacin (MIC 3.125 μgmL−1 against B. subtilis, E. coli, and K. pneumoniae). It was observed that compounds 4d and 4h displayed equipotent antibacterial efficacy against B. subtilis (MIC 3.125 μgmL−1) and S. aureus (MIC 6.25 μgmL−1). The studies demonstrated that the para-fluorophenylpiperazine substituted s-triazine (4n) was potent and exhibited broad spectrum antibacterial activity against S. epidermidis, K. pneumoniae, and P. aeruginosa with MIC of 6.25 μgmL−1 and for E. coli, it showed an MIC of 3.125 μgmL−1 equipotent with reference to the standard drug. Among all the compounds under investigation, compound 4g also demonstrated significant antifungal activity (3.125 μgmL−1) against C. albicans.

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