COX-1/COX-2 inhibition activities and molecular docking study of newly designed and synthesized pyrrolo[3,4-c]pyrrole Mannich bases |
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Authors: | Aleksandra Redzicka Łukasz Szczukowski Andrzej Kochel Benita Wiatrak Katarzyna Gębczak Żaneta Czyżnikowska |
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Affiliation: | 1. Department of Chemistry of Drugs, Wroclaw Medical University, Borowska 211, 50-556 Wroc?aw, Poland;2. Department of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 54-234, Wroc?aw, Poland;3. Department of Basic Medical Sciences, Wroclaw Medical University, Borowska 211, 50-556 Wroc?aw, Poland;4. Department of Inorganic Chemistry, Faculty of Pharmacy, Wroclaw Medical University, Borowska 211a, 50-556, Wroclaw, Poland |
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Abstract: | In the present paper we describe the biological activity of newly designed and synthesized series of pyrrolo[3,4-c]pyrrole Mannich bases (7a-n). The Mannich bases were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4–c]pyrrole scaffold (6a-c) with secondary amines and an excess of formaldehyde solution in C2H5OH. The chemical structures of the compounds were characterized by 1H NMR, 13C NMR, FT-IR, and elemental analysis. Moreover, single crystal X-ray diffraction has been recorded for compound 7l. All synthesized derivatives were investigated for their potencies to inhibit COX-1 and COX-2 enzymes by colorimetric inhibitor screening assay. In order to analyse the intermolecular interactions between the ligands and cyclooxygenase, experimental data were supported with the results of molecular docking simulations. According to the results, all of the tested compounds inhibited the activity of COX-1 and COX-2. |
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Keywords: | Corresponding author. Cyclooxygenase inhibition COX-1/COX-2 Molecular docking Mannich bases |
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