Synthesis of New Thiazole Derivatives Bearing Thiazolidin-4(5H)-One Structure and Evaluation of Their Antimicrobial Activity (original) (raw)
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Journal of Medicinal Chemistry, 2020
Thiazoles, their benzofused systems and thiazolidinone derivatives are widely recognized as nuclei of great value for obtaining molecules with various biological activities including analgesic, antiinflammatory, anti-HIV, antidiabetic, antitumor and antimicrobial. In particular, in the past decade many compounds bearing these heterocycles have been studied for their promising antibacterial properties due to their action on different microbial targets. Here we assess the recent development of this class of compounds to address mechanisms underlying antibiotic resistance at both bacterialcell & community levels (biofilms). We also explore the SAR and the prospective clinical application of thiazole and its benzofused derivatives, which act as inhibitors of mechanisms underlying antibiotic resistance in the treatment of severe drug-resistant infections. In addition, we examined all bacterial targets involved in their antimicrobial activity reporting, when described, their spontaneous frequencies of resistance.
Combinatorial chemistry & high throughput screening, 2015
As a part of our ongoing project on design and synthesis of new thiazole derivatives with antimicrobial activity fourteen new ethyl 2-(2-((E)-((Z)-5-(4-benzyliden)-4-oxothiazolidin-2-yliden)amino-4-yl)acetates , carrying halogens, methoxy and other groups were synthesized. Compounds were tested against eight Gram positive and negative bacteria as well as eight yeasts and mold by microdilution assay. All compounds showed good activity against all bacteria tested with MIC ranging between 2.3-39.8 μmol/ml x 10-2 and MBC of 9.2-79.6 μmol/ml x 10-2. As reference drugs Ampicillin (MIC 24.8-74.4 and MBC 37.2-124.0 μmol/ml x 10-2) and Streptomycin (MIC 4,3-17.2 and MBC 8.6-51.6 μmol/ml x 10-2) were used. The best activity was observed for 4-bromo derivative. All tested compounds showed excellent antifungal activity against all fungi tested with MIC in range between 0.3-38.6 μmol/ml x 10-2 and MFC range of 0.6-77.2 μmol/ml x 10-2, better than that of reference drugs, Ketoconazole (MIC 38.0-4...
SYNTHESIS, CHARACTERISATION AND INVITRO ANTIBACTERIAL SCREENING OF NOVEL THIAZOLE ANALOGUES
Thiazole containing N=C-S moiety exhibit broad spectrum of biological activities like fungicidal, antimicrobial, antitubercular activities and thiazole possess biological activities like bactericidal, antifungal, analgesic, antiinflammatory, diuretic, CNS depressant and anticancer activity. Recent literature reports explore the biological importance of thiazole analogues as antibacterial agent. The aim and objective of the present investigation is to develop novel thiazole analogues. In this study 3 novel thiazole analogues were synthesised by Schiff's reaction of 2-amino-4-phenylthiazole with substituted aromatic aldehydes. The puriy of newly synthesized compounds was ascertained by consistency in the TLC as well as melting point determination and were characterised by means of IR spectral analysis. Antibacterial screening was carried out using pour plate agar diffusion method and was tested against Bacillus subtilis, Staphylococcus aureus, E.coli, Pseudomonas aureginosa using Ciprofloxacin (100 µg/ml) as standard drug. Compound T1 exhibited significant activity towards gram positive organism and T2 exhibited significant activity towards gram negative organism when compared to standard drug Ciprofloxacin and others show moderate activity. Finally it was concluded that novel thiazole analogues can be considered as the future lead molecule for drug discovery process.
Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation
Molecules
Herein, we report computational and experimental evaluations of the antimicrobial activity of twenty one 2,3-diaryl-thiazolidin-4-ones. All synthesized compounds exhibited an antibacterial activity against six Gram-positive and Gram-negative bacteria to different extents. Thus, the MIC was in the range of 0.008–0.24 mg/mL, while the MBC was 0.0016–0.48 mg/mL. The most sensitive bacterium was S. Typhimurium, whereas S. aureus was the most resistant. The best antibacterial activity was observed for compound 5 (MIC at 0.008–0.06 mg/mL). The three most active compounds 5, 8, and 15, as well as compound 6, which were evaluated against three resistant strains, MRSA, P. aeruginosa, and E. coli, were more potent against all bacterial strains used than ampicillin. The antifungal activity of some compounds exceeded or were equipotent with those of the reference antifungal agents bifonazole and ketoconazole. The best activity was expressed by compound 5. All compounds exhibited moderate to goo...
Antimicrobial Prospect of Newly Synthesized 1, 3-Thiazole Derivatives
Molecules, 2011
A new series of 1,3-thiazole and benzo [d]thiazole derivatives 10-15 has been developed, characterized, and evaluated for in vitro antimicrobial activity at concentrations of 25-200 μg/mL against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram-ve organisms such as Escherichia coli (E. coli), and the fungal strain Aspergillus niger (A. niger) by the cup plate method. Ofloxacin and ketoconazole (10 μg/mL) were used as reference standards for antibacterial and antifungal activity, respectively. Compounds 11 and 12 showed notable antibacterial and antifungal activities at higher concentrations (125-200 μg/mL), whereas benzo[d]thiazole derivatives 13 and 14 were found to display significant antibacterial or antifungal activity (50-75 μg/mL) against the Gram+ve, Gram-ve bacteria, or fungal cells used in the present study. In addition, a correlation between calculated and determined partition coefficient (log P) was established which allows future development of compounds within this series to be carried out based on calculated log P values. Moreover, compounds 13 and 14 show that the optimum logarithm of partition coefficient (log P) should be around 4.
Asian Journal of Chemistry, 2017
New 2,3-substituted-1,3-thiazolidin-4-one (6a-f) were prepared by cyclocondensation of 2-[6-(4-chlorobenzyloxy)-2-naphthyliden]-4-(4-substituted phenyl)-5-methyl-1,3-thiazole (5a-f) and mercaptoacetic acid in benzene. The synthesized compounds were characterized on the basis of elemental analysis, 1 H NMR, 13 C NMR and FT-IR. The prepared compounds have been screened in vitro against two Grampositive Staphylococcus aureus, Staphylococcus epidermidis, and two Gram-negative Escherichia coli, Pseudomonas aernuginosa for antibacterial activity and two fungal strains Candida albicans, Candida krusei for antifungal activity using ciprofloxacin, ampicillin and ketoconazole with minimal inhibitory concentration (MIC) value of 10 mcg/L in DMSO. Compounds 6a and 6d showed good antibacterial and antifungal activities compared to reference medications utilized within this study.
Journal of Infection and Public Health, 2020
Background: The present work is an extension of ongoing efforts toward the development and identification of new molecules as monotherapy displaying anti-inflammatory and anti-infective activities and a wide-range of gastrointestinal selectivity. A series of novel set of trisubstituted thiazole compounds (AR-17a to AR-27a) have synthesized and evaluated for their in-vitro and in-vivo anti-inflammatory activities. Synthesized trisubstituted thiazole compounds were also evaluated for their potential antibacterial activity against clinical pathogens causing infectious disease. Material and Method: The structures of synthesized compounds were characterized by FTIR, 1 H NMR, Mass spectroscopic techniques and evaluated for their in-vitro and in-vivo anti-inflammatory effects using the human red blood cell (HRBC) membrane stabilization method and a carrageenan-induced rat paw oedema model, respectively, Diclofenac sodium and Ibuprofen were used as standard drugs. The synthesized compounds AR-17a to AR-27a screened for their in-vitro antibacterial activity against the gram-positive bacteria Staphylococcus aureus (ATCC25923) and Enterococcus faecalis (ATCC29212) and the gram-negative bacteria Escherichia coli (ATCC8739) and Pseudomonas aeruginosa (ATCC9027) using ciprofloxacin and cefdinir as standard drugs. Result: Compounds AR-17a and AR-27a elicited maximum anti-inflammatory activity, providing 59% and 61% protection at 20 mg/kg, respectively, in the inflamed paw model. Among the tested compounds, AR-17a (6.25), (54) and AR-27a (1.56), (52) had the least minimum inhibitory concentration values and the highest zone of inhibition, indicating their marked antibacterial activities. The lowest conc. were observed at 1.56, 6.25 g/mL for inhibition of bacteria by most of the compounds. Conclusion: Novel set of trisubstituted thiazole compounds (AR-17a to AR-27a) have synthesized and characterized successfully. The preliminary screening revealed that these compounds possess promising anti-inflammatory and antibacterial activities. In addition, the objective of the study was achieved with few of the promising structures like AR-17a to AR-27a, which are prove to be potential monotherapy candidates for the treatment of chronic inflammatory diseases and bacterial infections.
Letters in Drug Design & Discovery, 2018
Background: 2,4-disubstituted-1,3-thiazole derivatives (2a–j), (3a–f) and (4a–f) were synthesized, characterized and screened for their potential as antimicrobial agents. In the preliminary screening against a panel of bacterial strains, nine compounds showed moderate to potent antibacterial activity (IC50 = 13.7-90.8 μg/ml). Methods: In the antifungal screening, compound (4c) displayed potent antifungal activity (IC50 = 26.5 µg/ml) against Candida tropicalis comparable to the standard drug, fluconazole (IC50 = 10.5 µg/ml). Based on in vitro antimicrobial results, compounds 2f, 4c and 4e were selected for further pharmacological investigations. Hemolytic activity using human red blood cells (hRBCs) and cytotoxicity by MTT assay on human embryonic kidney (HEK-293) cells revealed non-toxic nature of the selected compounds (2f, 4c and 4e). To ascertain their possible mode of action, docking studies with the lead inhibitors (2f, 4c and 4e) were performed using crystal structure coordina...
Jurnal Teknologi, 2020
A series of thiazole derivatives 1-4 were synthesized employing simple one-pot reaction pathway and characterized via Fourier Transform Infrared (FTIR), Proton Nuclear Magnetic Resonance (1H NMR), Ultraviolet-Visible (UV-Vis) and Gas Chromatography-Mass Spectrometry (GC-MS). The newly synthesized compounds were evaluated for their in vitro antimicrobial properties against several bacterial strains including Gram-positive and Gram-negative as well as fungus using broth microdilution method. The results revealed that all of the compounds exhibited good activity with a range of MIC values between 1.25-5.0 mg/mL. From the MIC and MBC results, compound 1 exhibited good activities with same MIC value of 1.25 mg/mL and MBC value of 5 mg/mL against B. cereus and S. flexneri. In order to support antimicrobial results, the molecular docking studies were carried out for inhibition of the GlcN-6-P synthase as the target. Out of four compounds underwent for molecular docking studies, 5-acetyl-4-...
Molecules
Rapidly growing antimicrobial resistance among clinically important bacterial and fungal pathogens accounts for high morbidity and mortality worldwide. Therefore, it is critical to look for new small molecules targeting multidrug-resistant pathogens. Herein, in this paper we report a synthesis, ADME properties, and in vitro antimicrobial activity characterization of novel thiazole derivatives bearing β-amino acid, azole, and aromatic moieties. The in silico ADME characterization revealed that compounds 1–9 meet at least 2 Lipinski drug-like properties while cytotoxicity studies demonstrated low cytotoxicity to Vero cells. Further in vitro antimicrobial activity characterization showed the selective and potent bactericidal activity of 2a–c against Gram-positive pathogens (MIC 1–64 µg/mL) with profound activity against S. aureus (MIC 1–2 µg/mL) harboring genetically defined resistance mechanisms. Furthermore, the compounds 2a–c exhibited antifungal activity against azole resistant A. ...