New N-(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents (original) (raw)
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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.
SYNTHESIS, 2010
Cyclocandensation of 2-[(substitutedbenzylidene)amino]-4-(3-acetanilido)oxazoles (3a-3j) and 2-[(substitutedbenzylidene)amino]-4-(3-acetanilido)thiazoles (7a-7j) with chloroacetyl chloride give and N-2-[3chloro-4-(substitutedphenyl)-2-oxoazetidin-1-yl]-4-(3-acetanilido)oxazoles (4a-4j) and N-2-[3-chloro-4-(substitutedphenyl)-2-oxoazetidin-1-yl]-4-(3-acetanilido)thiazoles (8a-8j) respectively. N-2-[2-(substitutedphenyl)-4-oxo-1-thiazolidinyl]-4-(3-acetanilido)oxazoles (5a-5j) and N-2-[2-(substitutedphenyl)-4-oxo-1-thiazolidinyl]-4-(3-acetanilido)oxazoles (5a-5j) have been synthesized by reaction of compounds (3a-3j) and (7a-7j) with thioglycolic acid in presence of anhydrous zinc chloride. All the synthesized compounds were screened for their antibacterial activity and compared with reference drugs ampicillin and ciprofloxacin. The compound was the most potent compound of this series. Structure of all the synthesized compounds have been characterized by elemental (C, H, N) and spectral (IR and 1 H NMR) analysis.
Journal of Ultra Chemistry
In Present work, the Reduction of ethyl 2-(4-phenyl substituted)-4-methylthiazole-5-carboxylate(1) by Lithium Aluminium hydride in diethyl ether Solvent yield (2-(4-phenyl substituted)-4-methylthiazol-5-yl) methanol (2) followed by Oxidation using IBX in the DMSO solvent, to yield 2-(4-phenyl substituted)-4methylthiazole-5-carbaldehyde(3) which on further reaction with2-(4-phenyl substituted)-4-methylthiazole-5carbohydrazide(4) in the presence of conc. sulphuric acid in ethanol solvent to yield N-((2-(4-phenyl substituted)-4-methylthiazol-5-yl)methylene)-4-methyl-2-(phenyl substituted)thiazole-5-carbohydrazide(5) which further cyclisation with mercaptoacetic acid in presence of zinc chloride catalyst in DMF Solvent afforded series of thiazolidin-4-one derivatives namely N-(2-(2-(4-phenyl substituted)-4-methylthiazol-5-yl)-4-oxothiazolidin-3-yl)-2-(4-phenyl substituted)-4-methyl thiazole-5-carboxamide(6a-h). The structure of all the synthesized compounds was characterized by FT-IR, 1 H NMR, DIP MS data. Furthermore, compounds (6a-h) were screened for their antibacterial activity against gram negative (E. coli and P. aeruginosa) and gram positive (S. aureus and B. subtilis) bacteria, antifungal activity against pathogenic fungal strains and anti-inflammatory activities. Some of the compounds exhibited promising antibacterial, antifungal and anti-inflammatory activities.
Journal of the Korean Chemical Society, 2011
A series of isonicotinyl hydrazones and their 4-thiazolidinones have been synthesized by condensation of isonicotinic acid hydrazide with various aromatic aldehydes to yield Schiff's bases, followed by the cyclocondensation of Schiff's bases with 2-mercaptoacetic acid to yield their 4-thiazolidinones. The synthesized compounds have been characterized by their elemental, analytical and spectral studies. All these compounds were evaluated for their invitro antimicrobial activity against a spectrum of non-resistant and resistant microbial organisms. These studies proved that compounds 5e,i against B. subtilis; 5e,f,h against B. anthracis; 5g,i against S. aureus showed good activity at lower concentrations. Compounds 5d-5i displayed significant activity against resistant strain of K. pneumonia with minimum inhibitory potency in the concentration range of 2-16 ug/ml.
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.
Medicinal Chemistry Research, 2015
A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, 1 H NMR and 13 C NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC 50 = 8.0 lM).
Synthesis of some new 2, 3-diaryl-1, 3-thiazolidin-4-ones as antibacterial agents
Arkivoc, 2006
Some new 2,3-diaryl-1,3-thiazolidin-4-one derivatives having a 2,6-dichlorophenyl, antipyrine, or 1,2,4-triazole ring at N-3 and variously substituted 3-iodo-or 3-bromo-phenyl rings at C-2 have been synthesized and tested as antibacterial agents. The results of the in vitro tests showed that some of them have effective antibacterial activity.