Synthesis, Docking, and Evaluation of Antimicrobial Activity of a New Series of Acyclo C-Nucleosides of 1, 2, 4-Triazolo[4, 3- a ]quinoxaline Derivatives (original) (raw)
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Medicinal Chemistry Research, 2014
A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gramnegative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/ mL against Bacillus subtilis. To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of −7.73 and −95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of −4.55 and −101.56, respectively.
Design, Synthesis and Antibacterial Activity of some 3,6-Dimethlyquinoxaline-2-Hydrazone Derivatives
Journal of applied life sciences international, 2021
Aims: This aims of this study was to continue the effort to synthesis new quinoxaline-based heterocycles and study its antibacterial properties. Objective: This study was designed to reacts 3,6-dimethylquinoxaline-2-hydrazine with some substituted aromatic ketones and study their antibacterial properties on some locally and clinically isolated bacterial strains. Materials and Methods: Five 3,6-dimethylquinoxaline-2-hydrazone derivatives were synthesized from the reactions of 3,6-dimethylquinoxaline-2-hydrazine with various substituted aromatic ketones. The products were then tested for their potential antibacterial properties. Results: All the synthesized compounds were found to be active against all the bacterial strains investigated in this study. It was observed that the zones of inhibition observed for the synthesized compounds against the test organisms ranged between 15 mm and 38 mm. The MIC observed for the synthesized compounds ranged between 0.0313mg/mL and 0.125 mg/mL, while that of the standard antibiotic, streptomycin, varied between 0.0313 mg/mL and 0.500 mg/mL and those observed for tetracycline falls between 0.0313 mg/mL and 0.500 mg/mL. The minimum bactericidal concentrations exhibited by the synthesized compounds ranged between 0.0625 mg/mL and 0.250 mg/mL Discussion and conclusion: The study concluded that all the compounds exhibited appreciable bactericidal effects against all the bacterial strains, which is an indication that such Original Research Article
2016
A simple route for synthesizing tetrahydro-6-methylpyrimidine-one and – thione derivatives by condensation reaction of chloroquinolinecarbaldehyde. β-dicarbonyl compounds, as ethylacetoacetate or oracetylacetone and urea or thiourea in ethanol and acetic acid as a catalyst was used. On the other hand, pyroloquinolinone was obtained from the reaction of carbaldehydequinoline with formamide and fomic acid via Leuckart reaction. Moreover, chloroquinolinehydrazone was synthesized when carbaldehydequinoline reacted with hydrazine hydrate. Schiff base derivatives were prepared when chloroquinolinehydrazone was treated with substituted aldehydes. In addition 2-chloro-3-cyanoquinoline was prepared from dehydration of the aldoxime with thionyl chloride. Reaction of cyanoquinoline with hydrazine hydrate afforded 3-aminopyrazoloquinoline. This compound reacted with benzoylisocyanate and aldehyde derivatives to afford the corresponding N-(1H-pyrazolo[3,4-b]quinolone-3- ylcarbamoylbenzamide, N-(...
Aims: This aims of this study was to synthesis new quinoxaline-based heterocycles and study its antibacterial properties. Objective: This study was designed to synthesis some 3-methyl-6-nitroquinoxaline-2-one with hydrazine moiety, characterize the synthesized compounds, and study their antibacterial properties on some bacterial strains. Materials and Methods: Six 3-methylquinoxaline-2-hydrazone derivatives were synthesized by reacting 2-hydrazinyl-3-methyl-6-nitroquinoxaline with various substituted acetophenones. The hydrazones were screened for their potential antibacterial properties. Results: All the test compounds were found to possessed promising antibacterial properties against a panel of bacterial strains screened for this study. The MIC values exhibited by these compounds ranged between 0.0313 and 0.250 mg/mL. The lowest MBC of the compounds against the test organism was 0.0625 mg/mL while the highest MBC was 0.250 mg/mL. Discussion and Conclusion: The study concluded that all the compounds exhibited appreciable bactericidal effects against all the bacterial strains, which is an indication that such synthetic Original Research Article
3-(5-Mercapto-4-amino-1, 2, 4-triazol-3-yl) quinoxalin-2-ols were obtained from diethy 2-bromomalonate and o-phenylenediamine through multistep reactions. Ethyl 3-hydroxyquinoxaline-2-carboxylate on hydrazinolysis with substituted hydrazines resulted into 3-hydroxyquinoxaline-2-carbohydrazides (3a-g) which on reaction with CS 2 /KOH gave potassium 2-(3-hydroxyquinoxaline-2-carbonyl)hydrazine carbothioates (4a-g). Potassium 2-(3-hydroxyquinoxaline-2-carbonyl)hydrazine carbothioate (4a) on cyclization with substituted hydrazines gave 3-(5-mercapto-4-amino-1,2,4-triazol-3-yl)quinoxalin-2-ols (5a-g).The compounds were characterized by spectral analysis (1 H nuclear magnetic resonance [NMR], 13 C NMR, and mass spectrometry). Docking results are also presented for compounds 5a-g.
Journal of Heterocyclic Chemistry, 2017
Alkylation of quinoxaline scaffold 1 in the presence of K 2 CO 3 preferred N-alkylation than O-alkylation. Quinoxaline hydrazide 6 was successfully coupled with various amino acids, esters, and amines via azide-coupling method. New heterocyclic compounds containing quinoxaline linked to 1,3,4-oxadiazolethione or pyrazole were obtained from cyclization of 6 with CS 2 and acetylacetone, respectively. A series of hydrazide Schiff's bases were formed from hydrazide 6 by condensation with a set of aldehydes and ketones. NMR spectroscopy and mass spectrometry were used for structure elucidation of new compounds. The antimicrobial activity of the synthesized compounds was investigated toward two wild-type bacterial strains (Staphylococcus aureus and Escherichia coli) and two fungal species (Alternaria brassicicola and Fusarium oxysporum). Four compounds displayed a significant activity toward S. aureus. The ester 4 showed higher activity than the standard drugs, which make it a promising lead compound.
Scientia Pharmaceutica, 2004
A series of quinoxaline derivatives has been synthesized by reacting 3hydrazinoquinoxalines 1a,b with many bifunctional reagents. Reaction of 1a,b with chloroacetyl chloride and ethyl chloroacetate afforded 1-chloromethyl [I .2.4]tnazoIo[4.3-alquinoxalines 2a,b and dihydro[l,2,4]triazino[4,3-alquinoxalin-2-ones 3a,b respectively. Condensation of 1a,b with ethyl acetoacetate and acetylacetone yielded 2-quinoxalinylhydrazonobutanoates 4a,b and 2quinoxalinylhydrazono-2-pentanones 5a,b respectively. Cyclization of 5a,b gave 3,5-dimethylpyrazolylquinoxalines 6a,b. Moreover, reaction of compounds 2a,b with N-phenyl piperazine derivatives afforded 4-(4-Arylpiperazin-1-yl)-1-[(4arylpiperazin-1-yl) methyl)]triazoloquinoxalines 7a+. The prepared compounds were screened for In vitro antibacterial and antifungal activities. None of the tested compounds showed significant activity towards Pseudomonas aeruginosa. However, remarkable activities were noticed for compounds 5a and Sb against Eschenchia coli. Staphylococcus aureus and Candida albicans. Compounds 6a and 6b lacked any antimicrobial activities against the tested microorganisms.
Polycyclic Aromatic Compounds, 2020
In search of new active molecules, a small focused library of tetrazoloquinoline-based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be exhibiting promising antimicrobial and antioxidant activity characterized by their lower minimum inhibitory concentration values. All the synthesized compounds exhibited excellent antibacterial activity against Gram negative bacteria E. coli and F. devorans and antifungal activity against C. albicans and A. niger. Further, these compounds were tested for their antitubercular activity against dormant MTB H37Ra and dormant M. bovis BCG using XRMA assay protocol and showed no significant activity. Also, the synthesized compounds were found to have potential antioxidant activity with IC 50 range ¼ 12.48-50.20 lg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14a-demethylase, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole-incorporated tetrazoloquinolines may possess the ideal structural requirements for further development of novel therapeutic agents.
Design, Synthesis, Antibacterial Evaluation and Molecular Docking Studies of Some New Quinoxaline Derivatives Targeting Dihyropteroate Synthase Enzyme, 2018
Development of new antimicrobial agents is a good solution to overcome drug-resistance problems. From this perspective, new quinoxaline derivatives bearing various bioactive heterocyclic moieties (thiadiazoles, oxadiazoles, pyrazoles and thiazoles) were designed and synthesized. The newly synthesized compounds were evaluated for their in-vitro antibacterial activity against nine bacterial human pathogenic strains using the disc diffusion assay. In general, most of the synthesized compounds exhibited good antibacterial activities. The thiazolyl 11c displayed significant antibacterial activities against P. aeruginosa (MIC, 12.5 μg/mL vs levofloxacin 12.5μg/mL).Molecular docking studies indicated that the synthesized compounds could occupy both p-amino benzoic acid (PABA) and pterin binding pockets of the dihydropteroate synthase (DHPS), suggesting that the target compounds could act by the inhibition of bacterial DHPS enzyme. The results provide important information for the future design of more potent antibacterial agents.
Synthesis and antimicrobial activity of 1,2,3-triazoles containing quinoline moiety
Archives of Pharmacal Research, 2010
The synthesis and in vitro antimicrobial evaluation of several quinoline derivatives of glyoximes were described. Treatment of some aminoquinolines with anti-chloroglyoxime gave three new compounds as a ligand. The new ligands were characterized by elemental analyses, FT-IR and H-NMR. Their antibacterial 1 activities against five Gram-negative (Escherichia coli, Salmonella enteridis, Enterococcus faecalis, Klebsiella pneumonia and Pseudomonas aeruginosa) and four Gram-positive (Streptococcus mutans, Bacillus cereus, Staphylococcus aureus and Methicillin-resistant S. aureus) and antifungal activities against Candida albicans were measured by using disc diffusion and broth microdilution techniques. The minimum inhibitory concentration (MIC) values were calculated by microplate reader at 620 nm. It was found that N-(8-hydroxyquinolin-5-yl)-aminoglyoxime moderate antibacterial and antifungal activity against test microorganism including MRSA (Methicillin-resistant Staphylococcus aureus).