Синтез і антимікробна активність гексаметилен-N-малеїнімідопохідних спіроіндол- 3,3’-піроло[3,4-с]піролу

• Дата: 2017
• Автори: Suymka, Ye. I., Red’kin, R. G., Shemchuk, L. A., Hlebova, K. V., Filimonova, N. I.
• Формат: Стаття
• Мова: English
• Опубліковано: National University of Pharmacy 2017
• Теми: isatin; a-amino acids; bis-maleimide; spiro-2-oxindole; antimicrobial activity; UDC 547.752; 547.466; 615.281.9; изатин; α-аминокислоты; бис-малеинимид; спиро-2-оксиндол; антимикробная активность; УДК 547.752; ізатин; α-амінокислоти; біс-малеїнімід; спіро-2-оксіндол; антимікробна активність
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.17.929
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

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.