Submit Manuscript  

Article Details


Polyfunctionalized Pyrrole Derivatives: Easy Three-component Microwave-assisted Synthesis, Cytostatic and Antiviral Evaluation

[ Vol. 5 , Issue. 1 ]

Author(s):

Stella Manta, Niki Tzioumaki, Nikolaos Kollatos, Pelagia Andrea, Marili Margaritouli, Aggeliki Panagiotopoulou, Ioannis Papanastasiou, Christos Mitsos, Andrew Tsotinis, Dominique Schols and Dimitri Komiotis*   Pages 23 - 31 ( 9 )

Abstract:


Background: A large number of compounds with important biological properties contain the pyrrole heterocyclic system as main structural feature.

Methods: The synthesis of substituted pyrrole derivatives was carried out via a one-pot multicomponent reaction of sodium diethyl oxalacetate (3) with an equimolar amount of various aromatic aldehydes 1 and primary amines 2, in ethanol, using microwave irradiation. The newly synthesized compounds were evaluated for their potential cytostatic and antiviral activities in various cell culture lines.

Results: A range of novel pyrrole derivatives (4-13) were synthesized in a convenient one-step procedure. 3-Hydroxy-1-methyl-2-oxo-5-(3-chlorophenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester (9b) showed a noteworthy activity against leukemia, while all new pyrrole adducts were potent against the Yellow Fever Virus in Vero cells.

Conclusion: A new protocol, employing a three-component reaction under microwave irradiation, enabled the rapid synthesis of 3-hydroxy-2-oxopyrroles has been developed, providing access to compounds with significant antiviral activities.

Keywords:

Antiviral activity, cytostatic activity, multicomponent reaction, oxalacetate analogues, polyfunctionalized, pyrroles.

Affiliation:

Department of Chemistry, University of Cyprus, Nicosia, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, Institute of Biology, National Centre for Scientific Research "Demokritos", 15310 Ag. Paraskevi, Athens, School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimioupoli- Zografou, 15771 Athens, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa, School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimioupoli- Zografou, 15771 Athens, Rega Institute for Medical Research, Katholieke Universiteit Leuven, 3000 Leuven, Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa

Graphical Abstract:



Read Full-Text article