COX-1/COX-2 inhibition activities and molecular docking study of newly designed and synthesized pyrrolo[3,4-c]pyrrole Mannich bases
| Autor: | Łukasz Szczukowski, Żaneta Czyżnikowska, Aleksandra Redzicka, Benita Wiatrak, Katarzyna Gębczak, Andrzej Kochel |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Clinical Biochemistry
Pharmaceutical Science 01 natural sciences Biochemistry Mannich Bases chemistry.chemical_compound Structure-Activity Relationship Drug Discovery Cox 1 cox 2 Humans Cyclooxygenase Inhibitors Pyrroles Molecular Biology Cells Cultured Pyrrole chemistry.chemical_classification FORMALDEHYDE SOLUTION Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Intermolecular force Biological activity Carbon-13 NMR Combinatorial chemistry 0104 chemical sciences Molecular Docking Simulation 010404 medicinal & biomolecular chemistry Enzyme Cyclooxygenase 2 Drug Design Proton NMR Cyclooxygenase 1 Molecular Medicine |
| Zdroj: | Bioorganicmedicinal chemistry. 27(17) |
| ISSN: | 1464-3391 |
| Popis: | 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 theligands 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. |
| Databáze: | OpenAIRE |
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