Synthesis and Pharmacological Evaluation of Novel 1-(1,4-Alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted Urea Derivatives

Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics, Medical University of Lublin, 4a Chodźki St., Lublin PL-20093, Poland

School of Pharmacy, University of Eastern Finland, Yliopistonranta 1, P.O. Box 1627, Kuopio FI-70211, Finland

Department of Pharmacology and Pharmacodynamics, Faculty of Pharmacy with Division of Medical Analytics, Medical University of Lublin, 4A Chodźki St., Lublin PL-20093, Poland

Authors to whom correspondence should be addressed.

Academic Editor: Maria Emília de Sousa

Molecules 2016, 21(5), 582; https://doi.org/10.3390/molecules21050582

Received: 26 January 2016 / Revised: 25 April 2016 / Accepted: 27 April 2016 / Published: 30 April 2016

(This article belongs to the Section Medicinal Chemistry)

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Abstract

Novel 1-(1,4-alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted urea derivatives have been synthesized and evaluated for their central nervous system activity. Compounds 3a–m were prepared in the reaction between the respective 1-alkyl-4-aryl-4,5-dihydro-1H-imidazol-2-amines 1a–c and appropriate isocyanates 2 in dichloromethane. The compounds were subjected to in silico ADMET studies in order to select best candidates for in vivo experiments. The effects of the compounds on the spontaneous locomotor activity and amphetamine-evoked hyperactivity were estimated. Analgesic activity, without or in the presence of naloxone, was assessed in the writhing test. The tendency to change the HTR, evoked by l-5-HTP and the involvement in alteration in body temperature in mice was studied. Additionally, to check possible occurrence of drug-induced changes in the muscle relaxant activity of mice, which may have contributed to their behaviour in other tests, the rota-rod and chimney tests were performed. The new urea derivatives exerted significant activities in the performed pharmacological tests, although the presented results show a preliminary estimation, and thus, need to be extended for identification and understanding the complete pharmacological profile of the examined compounds. View Full-Text

Keywords: 1-alkyl-4-aryl-4,5-dihydro-1H-imidazo-2-amines; antinociceptive compounds; central nervous system (CNS) activity; in silico ADMET studies

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MDPI and ACS Style

Szacoń, E.; Rządkowska, M.; Kaczor, A.A.; Kędzierska, E.; Orzelska-Górka, J.; Fidecka, S.; Matosiuk, D. Synthesis and Pharmacological Evaluation of Novel 1-(1,4-Alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted Urea Derivatives. Molecules 2016, 21, 582. https://doi.org/10.3390/molecules21050582

AMA Style

Szacoń E, Rządkowska M, Kaczor AA, Kędzierska E, Orzelska-Górka J, Fidecka S, Matosiuk D. Synthesis and Pharmacological Evaluation of Novel 1-(1,4-Alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted Urea Derivatives. Molecules. 2016; 21(5):582. https://doi.org/10.3390/molecules21050582

Chicago/Turabian Style

Szacoń, Elżbieta, Marzena Rządkowska, Agnieszka A. Kaczor, Ewa Kędzierska, Jolanta Orzelska-Górka, Sylwia Fidecka, and Dariusz Matosiuk. 2016. "Synthesis and Pharmacological Evaluation of Novel 1-(1,4-Alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted Urea Derivatives" Molecules 21, no. 5: 582. https://doi.org/10.3390/molecules21050582

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Synthesis and Pharmacological Evaluation of Novel 1-(1,4-Alkylaryldisubstituted-4,5-dihydro-1H-imidazo)-3-substituted Urea Derivatives

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