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,
Andrey V. Smolobochkin,
Elizaveta A. Kuznetsova,
Dinara S. Abdullaeva,
Alexander R. Burilov,
Michail A. Pudovik,
Alexandra D. Voloshina,
Victor V. Syakaev,
Anna P. Lyubina,
Syumbelya K. Amerhanova,
Julia K. Voronina
Affiliations
Almir S. Gazizov
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Andrey V. Smolobochkin
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Elizaveta A. Kuznetsova
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Dinara S. Abdullaeva
Chemistry Department, Kazan Federal University, Kremlyovskaya Str. 18, 420008 Kazan, Russia
Alexander R. Burilov
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Michail A. Pudovik
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Alexandra D. Voloshina
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Victor V. Syakaev
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Anna P. Lyubina
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Syumbelya K. Amerhanova
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Str. 8, 420088 Kazan, Russia
Julia K. Voronina
N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Ave. 31, 119991 Moscow, Russia
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.
