DOI: https://doi.org/10.24959/ophcj.18.949

Synthesis and the study of the antimicrobial activity of N-aryliden-2-oxo-3,3-diphenil-2,3- dihydro-1H-thieno[3,4-b]pyrrol-6-carbohydrazides

K. M. Sytnik, T. P. Osolodchenko, S. V. Kolisnyk, Ye. I. Syumka

Abstract


Aim. To perform the synthesis of 2-oxo-3,3-diphenyl-2,3-dihydro-1H-thieno[3,4-b]pyrrol-6-carbohydrazide, its N-arylidene derivatives and study the antimicrobial activity of the compounds synthesized.
Results and discussion. 2-Oxo-3,3-diphenyl-2,3-dihydro-1H-thieno[3,4-b]pyrrol-6-carbohydrazide 2 was synthesized by the interaction of the starting ester 1 with hydrazine hydrate. The interaction of the former with arenecarbaldehydes (3.1-3.8) led to the corresponding N-arylidenes. The structure of the compounds obtained was proven by instrumental methods. The data of the antimicrobial activity screening confirmed the high activity of the compounds synthesized against Staphylococcus aureus and Candida albicans.
Experimental part. The synthesis of the starting and target compounds was performed under common conditions. The instrumental methods of analysis of organic compounds, and well agar diffusion method were used.
Conclusions. 2-Oxo-3,3-diphenyl-2,3-dihydro-1H-thieno[3,4-b]pyrrol-6-carbohydrazide and series of its N-arylidene derivatives have been synthesized, and their structure has been unambiguously proven. The antimicrobial activity of 2-oxo-3,3-diphenyl-2,3-dihydro-1H-thieno[3,4-b]pyrrol-6-carboxylic acid derivatives (1, 2) and N-aryliden-2-oxo-3,3-diphenyl-2,3-dihydro-1H-thieno[3,4-b]pyrrol-6-carbohydrazides (4.1-4.8) has been studied. Compounds possessing a high level of the antimicrobial activity against gram-positive bacteria – Staphylococcus aureus, Bacillus subtilis, as well as fungal species of Candida albicans have been found. The moderate activity of the compounds synthesized against gram-negative bacteria – Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa has been also proven.


Keywords


thieno[3,4-b]pyrrol; carboxylic acids hydrazides; antimicrobial activity

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