ELECTROCATALYTIC TANDEM ASSEMBLY OF ALDEHYDES WITH 2-THIOBARBITURIC ACID INTO 5,5'-(ARYLMETHYLENE)BIS(1,3-DIETHYL-2-THIOBARBITURIC ACIDS) AND EVALUATION OF THEIR INTERACTION WITH CATALASES

Авторы

  • Michail N. Elinson N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Anatoly N. Vereshchagin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Yuliya E. Ryzhkova N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Kirill A. Karpenko N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Fedor V. Ryzhkov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Mikhail P. Egorov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia

DOI:

https://doi.org/10.1007/5997

Ключевые слова:

aldehydes, 5, 5'-(arylmethylene)bis(1, 3-diethyl-2-thiobarbituric acids), 1, 3-diethyl-2-thiobarbituric acid, docking studies, electrocatalysis, electroorganic chemistry.

Аннотация

Electrocatalytic transformation of aldehydes with two equivalents of 1,3-diethyl-2-thiobarbituric acid has been carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of the substituted 5,5' -(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) in 87–98% yields and with 870–980% current efficiency. This new one-pot electrochemically induced tandem Knoevenagel–Michael process is a simple and efficient approach to substituted 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) containing two 1,3-diethyl-2-thiobarbituric acid fragments separated by C-aryl-substituted spacer, which are promising compounds for different biomedical applications, including anticonvulsant, antiAIDS agents and anti-inflammatory remedies. Theoretical studies were carried out to investigate the interaction of the synthesized compounds with beef and human catalases.

Загрузки

Опубликован

2021-03-15

Выпуск

Том 57 № 3 (2021)

Раздел

Оригинальные статьи