The Highly Regioselective Synthesis of Novel Imidazolidin-2-Ones via the Intramolecular Cyclization/Electrophilic Substitution of Urea Derivatives and the Evaluation of Their Anticancer Activity
Almir S. Gazizov, Аndrey V. Smolobochkin, E. A. Kuznetsova, Dinara S. Abdullaeva, А. Р. Бурилов, M. A. Pudovik, Alexandra D. Voloshina, Victor V. Syakaev, Anna P. Lyubina, Syumbelya K. Amerhanova, Julia К. Voronina
Abstract
A series of novel 4-(het)arylimidazoldin-2-ones were obtained by the acid-catalyzed reaction of (2,2-diethoxyethyl)ureas with aromatic and heterocyclic C-nucleophiles. The proposed approach to substituted imidazolidinones benefits from excellent regioselectivity, readily available starting materials and a simple procedure. The regioselectivity of the reaction was rationalized by quantum chemistry calculations and control experiments. The anti-cancer activity of the obtained compounds was tested in vitro.
Topics & Concepts
RegioselectivityChemistryElectrophilic substitutionIntramolecular forceElectrophileCombinatorial chemistryNucleophileSubstitution reactionNucleophilic substitutionElectrophilic aromatic substitutionUreaOrganic chemistryCatalysisOrganic and Inorganic Chemical ReactionsSulfur-Based Synthesis TechniquesSynthesis of heterocyclic compounds