N'-Benzylidene-N-(Thiazolyl)Acetohydrazide Derivatives: Synthesis and Antimicrobial Activity Evaluation (original) (raw)
Related papers
Journal of Enzyme Inhibition and Medicinal Chemistry, 2010
Some 4-[{1-(substituted)methylidine}-amino]-3-(4-pyridyl)-5-mercapto-4H-1,2,4-triazol (3a-3f) and N-[5-(4-substituted)-1H-1,2,3-triazol-1-yl]isonicotinamide derivatives (5a-5e) were synthesized by a sequence of reactions starting from isonicotinic acid hydrazide and is illustrated in scheme 1 and 2. The antibacterial and antifungal activities of newly synthesized compounds were tested by the disc diffusion method using nutrient agar medium against various microorganisms such as gram positive Staphylococcus aureus and Bacillus subtilis, gram negative Escherichia coli and the fungi Aspergillus niger and Candida albicans. Ciprofloxacin and Fluconazole at 50 μg/mL were used as standard drugs for antibacterial and antifungal activities, respectively. All the synthesized compounds showed significant activity against various microorganisms.
2015
Abstract: In this study, some novel N2-arylidene/cycloalkylidene-(6-(4-nitrophenyl)imidazo[2,1-b]thiazol-3-yl)acetic acid hydrazides (2a-d) were synthesized from (6-(4-nitrophenyl)imidazo[2,1-b]thiazol-3-yl)acetic acid hydrazide (1). The newly synthesized compounds were characterized by IR, 1H NMR, mass and elemental analysis. Their antibacterial and antifungal activities were evaluated against S. aureus ATCC 29213, P. aeruginosa ATCC 27853, E. coli ATCC 25922, C. albicans ATCC 10231, C. parapsilosis ATCC 22019, C. krusei ATCC 6258, T. mentagrophytes var. erinacei NCPF 375, M. gypseum NCPF 580 and T. tonsurans NCPF 245. N2-Cyclohexylidene-(6-(4-nitrophenyl)imidazo[2,1-b]thiazol-3-yl)acetic acid hydrazide (2c) and N2-(3-methylcyclohexylidene)-(6-(4-nitrophenyl)imidazo[2,1-b]thiazol-3-yl)acetic acid hydrazide (2d) showed the highest antibacterial activity. Particularly 2c showed the highest antifungal activity against tested fungi. Key words: Imidazo[2,1-b]thiazole, arylidene/cycloalk...
Il Farmaco, 1998
In this study 18 new hydrazones have been synthesized by reacting ortho-or para-substituted acetophenones with (3-substituted-1,2,4-triazol-5-yl-thio)acetohydrazide in ethanol. The prepared compounds were tested for antimicrobial activity. The prepared compounds exhibited only poor activity against Gram ( +) and Gram ( − ) bacteria with the minimal inhibitory concentration (MIC) ] 400 mg/ml. Moderate activity was observed against Candida species with MIC in the range 100 -400 mg/ml.
Synthesis and antibacterial activity of new substituted ethylidenehydrazinylidene-1,3-thiazol-4-ones
Journal of Chemical Research, 2014
A series of substituted ethylidenehydrazinylidene-1,3-thiazol-4-ones and dimethyl 2-{[4-1(-[5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-(thiazolidin-2-ylidene]hydrazonylidene}ethyl)phenyl]aminofumarate were synthesised by condensation of substituted ethylidene-N-phenylhydrazinecarbothioamides with dimethyl acetylenedicarboxylate. The synthesised compounds were characterised by spectroscopic methods and confirmed by single crystal X-ray crystallography. Some of the prepared compounds were screened for their in vitro antibacterial activity against different strains of microorganisms, compound 3b exhibited significant antibacterial activity against Pseudomonas aeruginosa compared to ciprofloxacin with MIC value of 1.12 µg mL-1 .
Synthesis, Characterization and Antimicrobial Activities of Some Thiazole Derivatives
In this work a series of thiazoles 9a-l were prepared by incorporation of pyrazoline ring at position 2 of 2-hydrazinyl-N-(4-phenylthiazol-2-yl) acetamide 8a-c by treating with chalcones 3a-d. The structures of the newly synthe-sized compounds were determined on the basis of their elemental analyses and spectroscopic data such as IR and HNMR spectra.The antimicrobial activity of isolated heterocyclic compounds was evaluated against Gram-positive, Gram-negative bacteria and fungi. Most of the compounds showed a moderate degree of potent antimicrobial activity.
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.
Arabian Journal of Chemistry, 2016
In this study, a series of novel thiazolidin-4-ones (5a-g) and azetidin-2-ones (6a-g) were synthesized from N-(6-chlorobenzo[d]thiazol-2-yl)hydrazine carboxamide derivatives of the benzothiazole class. Antimicrobial properties of the title compound derivatives were investigated against one Gram (+) bacteria (Staphylococcus aureus), three Gram (À) bacteria (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae) and five fungi (Candida albicans, Aspergillus niger, Aspergillus flavus, Monascus purpureus and Penicillium citrinum) using serial plate dilution method. The investigation of antibacterial and antifungal screening data revealed that all the tested compounds showed moderate to good inhibition at 12.5-200 lg/mL in DMSO. It has been observed that azetidin-2-ones derivatives are found to be more active than thiazolidin-4-ones derivatives against all pathogenic bacterial and fungal strains.
Synthesis and Evaluation of Novel Thiazole Derivatives
… on Synthetic Organic …, 2010
A vast array of thiazole derivatives having excellent broad spectrum activity forms an invaluable part of the present armory of the clinicians. The synthesis and antibacterial activity of several new ethyl 2-amino-4-methylthiazole-5-carboxylate(1) 5 derivatives substituted at 2 nd position by aryl aldehydes of the thiazole moiety have shown some to increase the antibacterial activity of thiazole. In this study we thought to synthesize thiazole system incorporating substituted aryl aldehydes. The most active compound was 4-methyl-5-hydrazine hydrate-2-(4-methoxy-3hydroxy benzene) methyleneamino thiazole-5-carboxylate (3c) equipotent to Ciprofloxacin.C 2 position of thiazole ring requires large hydrophilic, electronegative functional moieties like substituted phenyl ring etc for enhanced antibacterial activity of thiazole. In our compounds alkyl (methyl) group is present, still most of the compounds show good antibacterial activity.C 5 position of thiazole ring requires small hydrophobic, electronegative functional moieties like amino, hydrazine hydrate attach with ester for antibacterial activity of thiazole in general.
Synthesis and antimicrobial activity of some new hydrazone-bridged thiazole-pyrrole derivatives
Journal of Enzyme Inhibition and Medicinal Chemistry, 2013
A total of seventeen new N-substituted derivatives (2b-k and 3b-h) of 5-((2phenylthiazol-4-yl)methylene) thiazolidine-2,4-dione (2a) and 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione (3a) were synthesized. The structural elucidation of the newly synthesized compounds was based on elemental analysis, spectroscopic data (MS, 1 H NMR, 13 C NMR) and their antimicrobial activities were assessed in vitro against several strains of Gram-positive and Gram-negative bacteria and one fungal strain (Candida albicans) as growth inhibition diameter. Some of them showed modest to good antibacterial activity against Gram-negative E. coli, S. typhimurium and Gram-positive S. aureus, B. cereus, E. fecalis bacterial strains, while almost all the compounds were inactive against L. monocytogenes. All of the synthesized compounds showed moderate to very good activity against C. albicans.