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

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

Volume: 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*

Affiliation:

• Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Larissa,Greece

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

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.

Cite this article as:

Manta Stella , Tzioumaki Niki , Kollatos Nikolaos , Andrea Pelagia , Margaritouli Marili , Panagiotopoulou Aggeliki , Papanastasiou Ioannis , Mitsos Christos , Tsotinis Andrew , Schols Dominique and Komiotis Dimitri *, Polyfunctionalized Pyrrole Derivatives: Easy Three-component Microwave-assisted Synthesis, Cytostatic and Antiviral Evaluation, Current Microwave Chemistry 2018; 5 (1) . https://dx.doi.org/10.2174/2213335605666180221155915