I IN ND DO O A AM ME ER RI IC CA AN N J JO OU UR RN NA AL L O OF F STUDIES ON THE SYNTHESIS OF SOME NEW 1,2,4- TRIAZOLES DERIVATIVES AND EVALUATION FOR THEIR ANTI-FUNGAL ACTIVITY PROFILES (original) (raw)
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Archiv Der Pharmazie, 2008
A rapid and efficient one-pot condensation reaction of long-chain alkyl and alkenyl acid hydrazides and nitriles was carried out to afford 3,5-disubstituted-1H-1,2,4-triazoles. The compounds 5a–o were screened for in-vitro antibacterial activity against the representative panel of two Gram-positive and two Gram-negative bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungi. The various compounds show potent inhibitory action against test organisms. The compounds 5a–o were characterized on the basis of elemental analysis and spectral data.
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.
Novel 1, 2, 4-Triazoles as Antifungal Agents
BioMed Research International, 2022
The development of innovative antifungal agents is essential. Some fungicidal agents are no longer effective due to resistance development, various side effects, and high toxicity. Therefore, the synthesis and development of some new antifungal agents are necessary. 1,2,4-Triazole is one of the most essential pharmacophore systems between five-membered heterocycles. The structure-activity relationship (SAR) of this nitrogen-containing heterocyclic compound showed potential antifungal activity. The 1,2,4-triazole core is present as the nucleus in a variety of antifungal drug categories. The most potent and broad activity of triazoles have confirmed them as pharmacologically significant moieties. The goal of this review is to highlight recent developments in the synthesis and SAR study of 1,2,4-triazole as a potential fungicidal compound. In this study, we provide the results of a biological activity evaluation using various structures and figures. Literature investigation showed that...
Turkish Journal of Chemistry, 2007
A series of acylhydrazones (2a-d) was synthesized from the reactions of iminoester hydrochlorides (1a-e) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a-d) were obtained in the same reaction media. The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c). The acetylation of 4-amino-3-(4-hydroxyphenyl)-5-phenyl-4H-1,2,4-triazole (4a) produced 4amino-5-(4-acetoxyphenyl)-3-phenyl-4H-1,2,4-triazole (9), while the acetylation of 4-amino-3-(4-tolyl)-5-phenyl-4H-1,2,4-triazole (4b) gave 4-acetylamino-3-phenyl-5-(4-tolyl)-4H-1,2,4-triazole (10). The treatment of compound 4b with various aromatic aldehydes or acetophenone and 4-nitroacetophenone resulted in the formation of 4-arylidenamino-3,5-dialkyl-4H-1,2,4-triazoles (5a-e and 7a,b). Sodium borohydride reduction of 4-arylidenamino derivatives of 1,2,4-triazoles afforded 4-alkylamino-3,5-dialkyl-4H-1,2,4-triazoles (6a-e and 8a,b). All newly synthesized compounds were screened for their antimicrobial and antifungal activities using agar-well diffusion. Compounds 5c and 6d showed marginal antimicrobial activities against Staphylococcus aureus, while compound 6b displayed moderate antifungal activity towards Candida tropicalis.
A series of 4H-1,2,4-triazoles was synthesized by using aromatic acid precursors via conversion to corresponding hydrazides, then thiosemicarbazides and finally to 1,2, 4-triazole derivatives. The synthesized compounds were characterized through various instrumental techniques viz., FTIR, FT-NMR, and MS. All the compounds were tested against six different strains of bacteria and two different strains of fungi. Compound no.s 2, 3, 4, 7 & 8 showed remarkable activities against the test microorganisms. The MICs of the compounds were also determined and reported.
Synthesis and Biological Evaluation of Some New 1,2,3-Triazole Derivatives As Anti-microbial Agents
A series of 1,2,3-triazole derivatives bearing different chemical entities were prepared starting from 2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetohydrazide, compound 2. The purity of all new compounds was checked by TLC and elucidation of their structures was confirmed by IR, 1 H and 13 C NMR along with High Resolution Mass Spectrometry (HRMS). All the target compounds were evaluated for their possible antimicrobial activity. Most of the tested compounds showed moderate to good antibacterial activity against most of the bacterial strains used in comparison with ciprofloxacin as a reference drug. The most active compounds were 4a, 9a, 9b, and 9f. Results of antifungal activity revealed that most of the tested compounds showed a good antifungal activity in comparison to fluconazole as a reference drug. Compounds 4a, 9c, 9d and 9f were the most active ones.
A novel approach to the synthesis of 1,2,3-triazoles and their SAR studies
Medicinal Chemistry Research, 2010
A series of biologically active 4-acetyl-2-aryl-5-methyl-1-vinyl-2,3-dihydro-1H-1,2,3-triazole derivatives has been synthesized. The compounds were synthesized in excellent yields (80-85%) and the structures were established on the basis of corresponding IR, 1 H NMR, and elemental analysis data. The purity has been ascertained on the basis of chromatographic resolution using acetic acid-toluene (4:6 v/v) as binary eluent. All the compounds (4a-l) have been tested for their antifungal activity against a representative panel of fungal microbes. These synthesized compounds exhibited significant activities against A. niger, C. albicans, C. azyma, and A. flavus. For all the tests conducted, voriconazole was used as the control drug. The hydrophobic parameter (log P) also has been quantized for correlation of structure with biological activity, and a critical evaluation of structure-activity relationship (SAR) has been performed.
CERN European Organization for Nuclear Research - Zenodo, 2012
3-{4'-(Chlorobenzyloxy)-phenyl}-4-amino-5-mercapto-1,2,4-triazoles (la-d) were prepared by treating 4-(chlorobenzyloxy)-benzoylhydrazines successively with alcoholic potassium hydroxide-carbon disulphide and hydrazine hydrate, which on reaction with hydrazine hydrate, carbon disulphide, benzoic acid, benzoin, phenacyl bromide, phenyl isothiocyanate, formic acid, chloroacetyl chloride, benzaldehyde and isatin gave condensed bridgehead heterocycles (triazolo-thiadiazoles and triazolo-thiadiazines). The structures of the compounds were established with the help of elemental analysis and spectral data (IR, PMR and Mass). Compounds were screened for their antimycotic potential against human pathogenic fungi.
Journal of the Indian Chemical Society, 2012
3-{4'-(Chlorobenzyloxy)-phenyl}-4-amino-5-mercapto-1,2,4-triazoles (la-d) were prepared by treating 4-(chlorobenzyloxy)-benzoylhydrazines successively with alcoholic potassium hydroxide-carbon disulphide and hydrazine hydrate, which on reaction with hydrazine hydrate, carbon disulphide, benzoic acid, benzoin, phenacyl bromide, phenyl isothiocyanate, formic acid, chloroacetyl chloride, benzaldehyde and isatin gave condensed bridgehead heterocycles (triazolo-thiadiazoles and triazolo-thiadiazines). The structures of the compounds were established with the help of elemental analysis and spectral data (IR, PMR and Mass). Compounds were screened for their antimycotic potential against human pathogenic fungi.