Synthesis and the antimicrobial activity of hexamethylene-Nmaleinimidospiroindole- 3,3’-pyrrolo[3,4-c]pyrrole derivatives

Ye. I. Suymka, R. G. Red’kin, L. A. Shemchuk, K. V. Hlebova, N. I. Filimonova

Abstract


Aim. To synthesize a series of hexamethylene-N-maleinimidospiroindole-3,3’-pyrrolo[3,4-c]pyrrole derivatives, study the antimicrobial activity of the compounds synthesized and compare their antimicrobial activity with the antimicrobial activity of the bis-analogs previously synthesized.
Materials and methods. The methods of organic synthesis, instrumental methods for determination of the molecular structure of organic compounds, agar well diffusion method were used.
Experimental part. The interaction of isatins with a-amino acids and 1,6-bismaleinimidohexane in the equimolar ratio led to formation of 1′-(hexamethylene-N-maleinimido)-2a′,5a′-dihydro-1′H-spiroindol-3,3′-pyrrolo[3,4-c] pyrrol-2,2′,6′(1H,3′H,5′H)-trion derivatives. The structure of the compounds synthesized was reliably proven by the instrumental methods. Data of the microbiological screening showed a high level of the antimicrobial activity against Staphylococcus aureus and Candida albicans fungi.
Conclusions. It has been determined that the three-component condensation reaction of isatins with α-amino acids and 1,6-bismaleinimidohexane in the equimolar ratio is an efficient synthetic method of 1′-(hexamethylene-N-maleinimido)-2a′,5a′-dihydro-1′H-spiroindol-3,3′-pyrrolo[3,4-c]pyrrol-2,2′,6′(1H,3′H,5′H)-trion derivatives, which reveal a high level of the antimicrobial activity against Staphylococcus aureus and Candida albicans fungi. 1’-(Hexamethylene-N-maleiimido)-5’-methyl-2a’,5a’-dihydro-1’H-spiroindol-3,3’-pyrrolo[3,4-c]pyrrol-2,2’,6’(1H,3’H,5’H)-trione has shown the highest antimicrobial activity among derivatives of hexamethylene-Nmaleinimidospiroindol- 3,3’-pyrrolo[3,4-c]pyrrols.


Keywords


isatin; a-amino acids; bis-maleimide; spiro-2-oxindole; antimicrobial activity

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DOI: https://doi.org/10.24959/ophcj.17.929

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Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)