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.
Graphical Abstract
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