Synthesis and antimicrobial activity of some new 1,2,4-triazine and benzimidazole derivatives (original) (raw)
Related papers
Archives of pharmacal …, 2006
A novel series of 7,7-diphenyl-1,2-dihydroimidazo[2,1-c][1,2,4]triazin-6(7H)one 6a-h, were easily prepared via reactions of novel 2-hydrazinyl-4,4-diphenyl-1Himidazol-5(4H)-one (2) with hydrazonoyl halides 3a-h. In addition, we also examined the reaction of compound 2 with commercially available active methylene compounds to afford new pyrazoles containing an imidazolone moiety, expected to be biologically active. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1 H-NMR and mass spectral data. The antifungal and antibacterial activities of the newly synthesized compounds were evaluated.
European Journal of Medicinal Chemistry
Reaction of 2-guanidinobenzimidazole with halogenated active methylenes and ketones gave dihydroimidazole and 3,4-dihydrobenzo[4,5]imidazo [1,2-a][1,3,5]triazin derivatives in very good yield. The anti-bacterial evaluation of the newly synthesized products against broad spectrum of bacteria was performed. Most of products showed high inhibitory effect. All compounds have been characterized based on IR, 1H NMR, 13C NMR and Mass spectra.Reaction of 2-guanidinobenzimidazole with halogenated active methylenes and ketones gave dihydroimidazole and 3,4-dihydrobenzo [4,5]imidazo [1,2-a][1,3,5]triazin derivatives. The anti-bacterial evaluation of the synthesized products showed excellent zone of inhibition against tested bacteria.► Synthesis of dihydroimidzole and [1,3,5]triazins derivatives. ► All compounds good yields, short time and simplicity in the experimental procedure. ► The synthesized compounds showed excellent zone of inhibition against tested bacteria. ► All compounds have been characterized based on IR, 1H, 13C NMR, and mass spectrum.
ChemInform, 2003
A novel series of 7,7-diphenyl-1,2-dihydroimidazo[2,1-c][1,2,4]triazin-6(7H)one 6a-h, were easily prepared via reactions of novel 2-hydrazinyl-4,4-diphenyl-1Himidazol-5(4H)-one (2) with hydrazonoyl halides 3a-h. In addition, we also examined the reaction of compound 2 with commercially available active methylene compounds to afford new pyrazoles containing an imidazolone moiety, expected to be biologically active. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1 H-NMR and mass spectral data. The antifungal and antibacterial activities of the newly synthesized compounds were evaluated.
Journal of Chemistry, 2013
A study directed towards exploring the temperature-dependent reactivity of the chlorine atoms of 2,4,6-trichloro-s-triazine (TCT) in the nucleophilic displacement reaction, allowed a facile replacement of its chlorine atoms in succession with (i) N-amino methyl substituted isatin-3-hydrazones, (ii) N1-substituted-4-amino benzene sulphonamides, and (iii) 8-amino-4-oxo-N-benzyl-azacarbazole to produce the corresponding 2,4,6-trisubstituted-s-triazine, namely; 2-(N-amino methyl substituted isatin-3-hydrazinyl)-4-(N1-substituted-4′-amino benzenesulfonamidyl)-6-(8′-amino-4′-oxo-N-benzylazacarbazolyl)-1,3,5-triazine derivatives in acceptable yields. The compounds prepared were further evaluated for their antibacterial activity againstE. coliandB. subtilisand antifungal activities againstA. nigerandA. flavus, and some of them showed promising activity profile.
European Journal of Medicinal Chemistry, 2010
In this study 12 novel benzimidazole compounds bearing hydrazone moiety were synthesized in order to investigate their possible antibacterial and antifungal activity. Structures of the synthesized compounds were elucidated by spectral data. Six different gram-negative and four different gram-positive bacterial strains were used in antibacterial activity tests. Antifungal activity tests were also performed against three different fungal strains. Most of the test compounds found to be significantly effective against Proteus vulgaris, Staphylococcus typhimurium, Klebsiella pneumoniae and Pseudomonas aeruginosa gramnegative bacterial strains. A structureeactivity relationship (SAR) study including some electronic parameters was carried out and a connection between antibacterial activity and electronic properties of the target compounds was determined. Toxicity of the most effective compounds was established by performing BrineeShrimp lethality assay.
Synthesis of Some New Benzimidazole Acid Hydrazide Derivatives as Antibacterial Agents
Indian Journal of Heterocyclic Chemistry, 2018
An efficient synthesis of some new benzimidazole derivatives linked to various heterocyclic scaffolds was performed by multistep reaction sequences. The structures of synthesized compounds were elucidated by spectral studies (infrared, nuclear magnetic resonance [ 1 H NMR], 13 C NMR, and mass spectrometry). The compounds were evaluated for their antibacterial activity against few Gram-positive and Gram-negative bacteria. Among the screened compounds, compound 7 showed the most potent inhibitory activity.
Rasayan Jouranal of Chemistry http://www.rasayanjournal.com Vol.3, No.1 (2010),51-54, 2010
The novel reaction of 3-(2-methylbenzimidazol-1-yl) propanoic acid hydrazide with CS2/KOH gave Oxadiazole derivative which under went Mannich reaction to give 3-[(dialkylamino) methyl]-2phenyl-4(3H)-quinazolinone. All compounds were characterized by physical, chemical, analytical and spectral data. All compounds have been screened for their antimicrobial activity and anti-inflammatory activity. Keywords: 4(3H)-Quinazolinones,Niementowski Reaction, N-Mannich reaction, Antimicrobial agent.
European Journal of Medicinal Chemistry, 2009
a b s t r a c t 5-Pyridin-4-yl-1,3,4-oxadiazole-2-thiol (2) was obtained from the reaction of isonicotinic acid hydrazide with carbon disulfide in basic media and converted into 4-amino-5-pyridin-4-yl-4H-1,2,4triazole-3-thiol (5) by the treatment with hydrazine hydrate. The synthesis of 3 and 6 was performed from the reaction of 2 and 5 with ethyl bromide. The treatment of 5 with 4-fluorobenzaldehyde or indol-3-carbaldehyde resulted in the formation of 4-[(arylmethylene)amino]-5-pyridin-4-yl-4H-1,2,4triazole-3-thiols (7a and 7b). The reactions of 2, 5 and 7a with some primary and secondary amines in the presence of formaldehyde afforded the corresponding Mannich bases, 4a, 4b, 9a-9c and 8.