The synthesis, physico-chemical properties, the antibacterial and antifungal activity of 2-[(5-(adamantane-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide ylidene derivatives

V. M. Odyntsova

doi:10.24959/ophcj.17.912

Authors

V. M. Odyntsova Zaporizhzhia State Medical University, Ukraine

DOI:

https://doi.org/10.24959/ophcj.17.912

Keywords:

1, 2, 4-triazole, IR-, NMR 1H-spectroscopy, chromatography mass spectra, acetohydrazides, antimicrobial and antifungal activity

Abstract

One of the main stages for creating a drug is the synthesis of a promising substance. The combination of adamantane and 1,2,4-triazole in one molecule provides the fertile ground for the synthesis of new compounds with low toxicity and a pronounced pharmacological activity.

Aim. To synthesize 2-[(5-(adamantane-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide ylidene derivatives, study their physico-chemical properties, the antimicrobial and antifungal activity.

Results and discussion. During the synthetic part of our work the aldehyde selection was based on the presence of various substitutes in the aromatic or heterocyclic nuclei. Benzaldehyde and its fluorine-, bromine-, hydroxy-, nitro-, methoxy-, dimethylamino- and dimethoxy- substituents were used. Furan-2-carbaldehyde, 5-nitrofuran-2-carbaldehyde, pyridine-2-ylcarbaldehyde and pyridine-3-ylcarbaldehyde were used among heterocyclic aldehydes. The structure of the synthesized compounds was confirmed by modern complex physico-chemical methods of analysis, elemental analysis, IR, NMR 1H-spectroscopy, and their individuality was proven by HPLC-MS. In the course of the initial screening of the antimicrobial activity of the ylidene derivatives of 2-[(5-(adamantane-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide synthesized it was found that the compounds obtained revealed a moderate antimicrobial and antifungal activity.

Experimental part. Ylidene derivatives of 2-[(5-(adamantane-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide were obtained by the reaction of nucleophilic addition of the hydrazide fragment of the aldehyde group carbonyl. The antimicrobial and antifungal activities were determined by serial two-fold dilution in the liquid nutrient media. To compare the antimicrobial activity of the compounds studied trimethoprim was used as a reference drug.

Conclusions. New ylidene derivatives of 2-[(5-(adamantane-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]acetohydrazide have been synthesized; their structure has been determined by modern physico-chemical methods of analysis (elemental analysis, IR- and NMR 1H-spectroscopy), and their individuality has been confirmed by HPLC-MS. Among the compounds synthesized the substances with the antimicrobial and antifungal action that is similar or in some cases even exceed the action of the reference drug trimethoprim have been found. The compound 2-[(5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazole-3-yl)thio]-N’-(4-hydroxybenzyliden)acetohydrazide appeared to be more active than the reference drug in relation to E. coli and S. aureus.

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