Synthesis and Antimicrobial Evaluation of Some New Thiazole, Thiazolidinone and Thiazoline Derivatives Starting from 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde (original) (raw)
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CHEMICAL & PHARMACEUTICAL BULLETIN, 2010
Pyrazole and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activities, including antibacterial, 1) antifungal, 2) herbicidal, 3) insecticidal 4) and other biological activities. Similarly, the biological activities of various 1,2,4-triazole derivatives and their N-bridged heterocyclic analogs have been widely investigated as antitumor, 8) antiviral, 9) anti-inflammatory, 10) analgesic 11) and antidepressant. 12) 1,2,4-Triazole system is also an important starting material in the synthesis of biologically active heterocycles, which constitute an important class of organic compounds with diverse biological activities, including antiparasitic, analgesic, antibacterial and anti-inflammatory activities. Further, triazole fused with other heterocyclic rings is also found to possess diverse applications in the field of medicine. The commonly known systems are triazolo-pyridines, 19) triazolo-pyridazines, 20) triazolo-pyrimidines, 21) triazolo-pyrazines, 22) triazolo-triazines 21) and triazolo-thiadiazines. 23) In addition, it has been reported that thiadiazoles exhibit a broad spectrum of biological effectiveness such as anti-parkinsonism, 24) hypoglycaemic, 25) anticancer, 26) anti-inflammatory, 27) anti-asthmatic 28) and anti-hypertensive 29) activities.
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.
Russian Journal of Bioorganic Chemistry, 2020
3-(2-Thienyl)-5-aryl-1-thiocarbamoyl-2-pyrazolines were reacted with chloroacetone derivatives and hydrazonyl chloride derivatives in ethanol to afford the corresponding thiazolylpyrazoline derivatives and thiophenylpyrazolyl-5-substituted aryl-diazenylthiazole derivatives, respectively. The structures of the newly synthesized compounds were elucidated by different elemental and spectral analyses (IR, mass, 1 H and 13 C NMR). The antimicrobial and antifungal activities of the newly synthesized compounds were evaluated against four bacterial species and five fungal strains. In addition, the antitumor activities of two of the newly synthesized compounds 1-(2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-methyl thiazol-5-yl)ethan-1-one and 2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methyl-5-(phenyl-diazenyl)thiazole against HEPG-2, HCT-116, MCF-7, BHK, and CACO-2 were evaluated. From the obtained results, we found that these two compounds were the most potent candidates towards all gram-positive and gram-negative bacteria, as well as the fungi studied. Also, the same two compounds showed strong antitumor activities against two of the tumor cell lines (HCT-116 and CACO-2).
Pharmacologyonline
Recent observations of literature suggests that molecular manipulation, combination of two or more active moieties into one molecule and synthesis of totally newer moieties have been the method of research. In view of this we have undertaken synthesis of various 6-(pyrazin-2-yl)-3-substituted [1,2,4]triazolo[3,4b][1,3,4]thiadiazole derivatives and their antibacterial and antifungal activity. The Structures of the synthesized compounds were established with spectral characterizations using UV, IR, 1 H-NMR and mass spectra. The Synthesized molecules were tested against bacterial strains (Micrococcus luteus, Bacillus subtilis, Bacillus cereus, Enterobacter aerogenes, E. Coli, Klebsiella pneumonia, Proteus microbilis, Pseudomonas aeruginosa and Staphylococcus aureus, Salmonella typhii, Streptococcus pneumoniae), fungal strains (Candida albicans, Cryptococcus albidus, Trychophyton rubrum, Apergillus niger, A. flavus, A. spinulosus, A. terrcues and A. nidulans) by agar diffusion method. The results of preliminary screening showed that all synthesized 6-(pyrazin-2-yl)-3-substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has good antibacterial activity against all strains but only few of them showing good activity against Streptococcus pneumoniae. Similarly some of these molecules showed good antifungal activity against all strains except against trychophyton species.
Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities
Journal of Heterocyclic Chemistry, 2019
A series of novel thiazolyl pyrazolines 7a‐h, 9a‐f, and 11a‐f have been synthesized by the reaction of thioamide derivatives 5a,b with 1‐aryl‐2‐bromoethanones 6a‐d, chloroacetones 8a‐c, and hydrazonoyl chlorides 10a‐c. Additionally, pyrazoles 15a‐c and 20 were prepared starting from enaminone 13. These newly synthesized compounds were screened for their in vitro antibacterial activity against four bacterial species. Compound 11b showed a moderate activity against Klebsiella pneumoniae. Compounds 7c and 11c revealed a moderate activity against Pseudomonas aeruginosa. In addition, the antifungal activity of the newly synthesized compounds was determined against five fungal strains. Compounds 7e, 7g, and 11e showed a good activity against Aspergillus flavus and Penicillium expansum.
SYNTHESIS AND ANTIMICROBIAL PROPERTIES OF SOME THIAZOLE AND PYRIDINE DERIVATIVES
It was confirmed, that by condensation of thiosemicarbazide derivative of camphor with phenacyl bromide in ethanol and at the presence of piperidine, the corresponding thiazole derivatives are formed. By the interaction of camphor's thiosemicarbazide derivative with methyl ester of α-bromoacetic acid in the same reaction conditions, the corresponding thiazolidone derivative was synthesized. The way of synthesis of benzylamine the iminopyridine derivative by the one-pot three-component reaction of pbromobenzylidene malononitrile with malononitrile has been developed. Synthesized pyridine derivative demonstrates high antimicrobial activity. Structures of all synthesized compounds confirmed by NMR spectroscopy.
Synthesis and Antimicrobial Profile of Some Newer Heterocycles Bearing Thiazole Moiety
SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY, 2012
Various substituted acetophenones on treatment. with iodine and thiourea yielded 2-amino-4-( substituted-phenyl)-thiazole, which on further treatment with acetic anhydride generated N-(4-(substituted phenyl)thiazol-2-ylacetamide(1-5). All the synthesized compounds were characterized by their respective FTIR, 1H NMR, and mass data. Synthesized compounds (l, 2, 3, 4, 5) when subjected to investigation for their antimicrobial activities i.e. antibacterial and antifungal studies against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, Aspergillus flavus, and Aspergillus fumigatus by disk diffusion method, revealed that compound 2 deemed to be most potent with the largest zone of inhibition.
2009
Summary Recent observations of literature suggests that molecular manipulation, combination of two or more active moieties into one molecule and synthesis of totally newer moieties have been the method of research. In view of this we have undertaken synthesis of various 6-(pyrazin-2-yl)-3-substituted [1,2,4]triazolo[3,4b][1,3,4]thiadiazole derivatives and their antibacterial and antifungal activity. The Structures of the synthesized compounds were established with spectral characterizations using UV, IR, 1 H-NMR and mass spectra. The Synthesized molecules were tested against bacterial strains (Micrococcus luteus, Bacillus subtilis, Bacillus cereus, Enterobacter aerogenes, E. Coli, Klebsiella pneumonia, Proteus microbilis, Pseudomonas aeruginosa and Staphylococcus aureus, Salmonella typhii, Streptococcus pneumoniae), fungal strains (Candida albicans, Cryptococcus albidus, Trychophyton rubrum, Apergillus niger, A. flavus, A. spinulosus, A. terrcues and A. nidulans) by agar diffusion m...
Anti-Infective Agents, 2014
In search of new antimicrobial agents with improved potency, we have synthesized a series of N-substituted thiazolidinedione-pyrazole based 3-(3-(1H-pyrrol-1-yl)propyl)-5-((3-(substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene)thiazolidine-2,4-diones (6a-j) in two successive steps. Initial step involves Knoevenagel type condensation of 3-(substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehydes (2a-j) with thiazolidine-2,4-dione (3) to furnish intermediate compounds (4a-j). Finally, target compounds (6a-j) were achieved via one-pot reaction of compounds (4a-j), 1,3-dibromopropane and 1H-pyrrole (5). The chemical structures of all the newly synthesized compounds were established based on IR, 1 H NMR, 13 C NMR and mass spectra. All the synthesized compounds (4a-j, 6a-j) were evaluated for their in vitro antimicrobial activity.