Synthesis and antibacterial activities of 5-subsituted-4-amino-1,2,4-triazole-3-thiols. (original) (raw)
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The use of 4-amino-5-benzyl-4H-[1,2,4]triazole-3-thiol (1) as a precursor to synthesize some new biologically active heterocycles has been found to be effective. Condensation of 1 with appropriate aldehydes gave the new Schiff bases 2a, b, which either by cyclization with thioglycolic acid gave 3a, b, or by Mannich reaction using morpholine gave 4a, b. Reaction of 1 with different halogen compounds such as, benzenesulphonyl chloride, chloroacetamide, chloroacetone, phenyl acetyl chloride, chloroacetic acid, oxalyl chloride and dichloroacetic acid afforded the newly compounds 5, 6, 7, 8, 9, 10 and 11 respectively. The chemical structures of the prepared compounds were characterized by considering the data of their elemental analyses as well as their spectral data of their FT-IR, 1H NMR, 13C NMR and Mass spectra. Investigation of the antibacterial activity of these compounds was done by the paper disc technique. Some of the tested compounds showed high and favorable antibacterial activity.
Istanbul university journal of pharmacy, 2023
Background and aims: The discovery of new antifungals and antimicrobials to overcome resistance has always been a crucial topic for sustainable world health. Since sulfur-containing triazole heterocycles derivatives have shown greater interest due to their valuable applications, we reported herein, the synthesis of some mercaptotriazole derivatives to discover underlying structural requirements for antimicrobial and antifungal activity. Methods: Firstly, the benzoic acid hydrazide was synthesized. Then it was reacted with carbon disulfide in the solution of alkali ethanol to give potassium dithiocarbazinate salt. Then the basic nucleus 4-amino-5-phenyl-1-4H-1,2,4-triazole-3-thiol was prepared by cyclization of potassium salt with hydrazine hydrate. After that, a condensation reaction with different aldehydes was conducted to synthesize Schiff bases, which were cyclized by treating with thioglycolic acid to prepare desired compounds. Results: All the synthesized compounds were confirmed by their melting point, FTIR, 1H-NMR, and 13C-NMR spectra, elemental analysis was determined for their antimicrobial activity by using a simple susceptibility screening test with agar-well diffusion. Few compounds showed promising activity against bacteria and yeast-like fungi. Conclusion: 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol derivatives proved promising antimicrobial activities.
Al Mustansiriyah Journal of Pharmaceutical Sciences
New series of tricyclic benzo[d]thiazole derivatives (2-12) incorporated into fused to different five membered nitrogen and sulphur containing heterocyclic were prepared from 2- hydrazinobenzo[d]thiazole (1) when treated with triethylformate, acetic anhydride, ethyl chloro acetate, carbon disulphide in alkali, and urea respectively.Compound(1) converted to Schiff’s bases by the condensation different aromatic aldehydes, the synthesized Schiff’s bases were cyclized by bromine in acetic acid to form triazole ring in the new derivatives (7-11) , which might result in biologically active agents.Similar new tricyclic compounds, triazolobenzothiazol-3-amine [12], was obtained from action of benzo[d]thiazole-2-thiol with thiosemicarbazide. The structures of the new compounds have been characterized by elemental analysis and spectral data.Newly synthesized compounds (2-12) were screened for their antibacterial activity against four bacterial species. They were found to exhibit good antibact...
Medicinal Chemistry Research, 2010
A series of novel 1,2,4-triazole derivatives have been synthesized by condensing the methyl benzoate and methyl salicylate with various substituents; their structures were established on the basis of elemental analysis, Fourier transform infrared spectroscopy (FTIR), 1 H nuclear magnetic resonance (NMR), and mass spectral data. All title compounds were subjected to in vitro antibacterial and antifungal screening against four different bacterial and fungal strains. Preliminary results indicate that some of them exhibit promising activities and deserve further consideration as potential antimicrobials.
Synthesis, Characterization and Evaluation of Anti-microbial activity of some novel 1,2,4-triazoles
Some novel 4-(aryliidineamino)-5-(1-(4-isobutylphenyl) ethyl)-4-yl-4H-1,2,4-triazole-3-thiols were prepared from the reaction of carbon-di-sulphide and hydrazine hydrate in water to produce thiocarbohydrazides. The thiocarbohydrazides is then refluxed with ibuprofen for 2 hour, followed by cooling to room temperature and washing with sodium bicarbonate solution to produce 5-(1-(4-isobutylphenyl) ethyl)-4H-1,2,4-triazole-3-thiole. It is then refluxed with different aldehydes in the presence of ethanol and HCl to produce the title compounds. The synthesized compounds are recrystallized from ethanol and are analyzed for their physical and spectral data. They are screened for their anti-microbial activity and it was found that the title compounds are found to have moderate to good antimicrobial activity.
2014
Objectives: To synthesize, characterize and evaluate antimicrobial properties of some 1, 2, 4-triazole derivatives. Methods: A novel series of 1, 2, 4-Triazole derivatives (D-1-D-8) had been synthesized. Ethyl esters of benzoic and 4-substituted benzoic acids were synthesized using ethanol and conc. sulphuric acid. In the second step, hydrazides of these esters were prepared. This hydrazide was converted into potassium salt of dithiocarbazinate using carbon disulfide and potassium hydroxide which on cyclization formed compounds (D-1-D-2). Compound D-3 was formed by reacting D-1 with 4-methylbenzenesulfonyl chloride in dry pyridine. Compounds (D-4-D-8) were synthesized by mixing aqueous solution of 10% NaOH in different primary amines and then heating it with potassium salt of dithiocarbazinate. The structures of newly synthesized compounds were established on the basis of 1 Results: The results revealed that compounds D-3 and D-4 exhibited good antibacterial activity and D-1 and D-2...
Design, synthesis and evaluation in vitro antibacterial activity of new 1,2,3-triazole derivatives
PROCEEDING OF THE 1ST INTERNATIONAL CONFERENCE ON ADVANCED RESEARCH IN PURE AND APPLIED SCIENCE (ICARPAS2021): Third Annual Conference of Al-Muthanna University/College of Science
In the current work, 1,2,3-triazole and 1,3,4-thiadiazole rings were combined in the same structure via a multisteps synthetic pathway to present a series of 1,2,3-triazole derivatives. The newly synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR and mass spectra. The final compounds and their precursors were in vitro tested as antibacterial agents by well diffusion method against the Gram-negative strains (Helicobacter Pylori, Klebsiella pneumonia, Escherichia coli O157) and the Gram-positive strain of Staphylococcus aureus. The bioassay indicated that all the tested compounds were not active or possessed a week to excellent antibacterial activity depending on the type of the tested bacteria and the structure of the target compounds.
Design and Synthesis of Some New 1,2,4-TRIAZOLE Derivatives as Potential Antibacterial Agents
Triazoles with different substituent groups are found to possess diverse applications in the field of medicinal chemistry. A new series of novel 1,3,5-trisubstituted[1,2,4]triazole derivatives, their Schiff bases and their amide derivatives were synthesized. Schiff bases (6-10) were prepared by the reaction of the triazoles amine 5 with equimolar amounts of the appropriate substituted benzaldehydes. The amide derivatives (25-39) were obtained by condensation of triazole amines (21-24) with the appropriate acid chloride. Chemical structures were confirmed by IR, 1H-NMR, 13C-NMR, FAB-MS, EI-HRMS spectra and elemental analyses. All the newly synthesized compounds were tested for in vitro activity against certain strains of bacteria such as Staph. aureus, Staph. saprophyticus, Escherichia coli and Bacillus cereus. Most of the tested new compounds exhibited promissing antibacterial activity. Some of them showed antibacterial activity more significant than the reference drugs. Compounds 6...
Synthesis and in Vitro Biological Activities of 4,5-Disubstituted 1,2,4-Triazole-3-Thiols
Advances in Microbiology, 2013
The triazole nucleus is an important part of the therapeutically interesting drug candidate as antimicrobial, analgesic, anticancer, anticonvulsant and anti-inflammatory agents. Methods: Therefore, in this study, twelve 4,5-disubstituted-1,2,4-triazole-3-thiols were synthesized by the reaction of substituted isothiocyanates and hydrazides using the common method of base catalysed intramolecular dehydrative cyclization of substituted thiosemicarbazides 3(a-f) and 4(a-f). The structures of these compounds were characterized by means of FT-IR, 1 H-NMR, and elemental analysis data. All these compounds were screened for antibacterial, antioxidant, antitumor and cytotoxic activities. Results: Among these compounds: 5c, 5f and 6f were found active against gram positive cocci, the compounds 5a, 5b, 5d, 6a and 6f showed 85% free radical scavenging effect at 3 ppm when tested for antioxidant activity, 75% tumors inhibition was recorded using 5c, 5d and 6a and brine shrimps lethality assay declared 5a, 5b and 6d was 129.62 µg/ml, 161.577 µg/ml and 81.56 µg/ml respectively. Conclusion: Compounds carrying significant bioactivity can be further studied using animal models to establish their safety profile prior to initiating clinical trials.