Cargando…

Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents

In the present paper, we describe the biological activity of the newly designed and synthesized series N-substituted 3,4-pyrroledicarboximides 2a–2p. The compounds 2a–2p were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4-c]pyrrole scaffold (1a–c) with secondary amin...

Descripción completa

Detalles Bibliográficos
Autores principales: Redzicka, Aleksandra, Czyżnikowska, Żaneta, Wiatrak, Benita, Gębczak, Katarzyna, Kochel, Andrzej
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7866801/
https://www.ncbi.nlm.nih.gov/pubmed/33573356
http://dx.doi.org/10.3390/ijms22031410
_version_ 1783648157873209344
author Redzicka, Aleksandra
Czyżnikowska, Żaneta
Wiatrak, Benita
Gębczak, Katarzyna
Kochel, Andrzej
author_facet Redzicka, Aleksandra
Czyżnikowska, Żaneta
Wiatrak, Benita
Gębczak, Katarzyna
Kochel, Andrzej
author_sort Redzicka, Aleksandra
collection PubMed
description In the present paper, we describe the biological activity of the newly designed and synthesized series N-substituted 3,4-pyrroledicarboximides 2a–2p. The compounds 2a–2p were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4-c]pyrrole scaffold (1a–c) with secondary amines and an excess of formaldehyde solution in C(2)H(5)OH. The structural properties of the compounds were characterized by (1)H NMR, (13)C NMR FT-IR, MS, and elemental analysis. Moreover, single crystal X-ray diffraction has been recorded for compound 2h. The colorimetric inhibitor screening assay was used to obtain their potencies to inhibit COX-1 and COX-2 enzymes. According to the results, all of the tested compounds inhibited the activity of COX-1 and COX-2. Theoretical modeling was also applied to describe the binding properties of compounds towards COX-1 and COX-2 cyclooxygenase isoform. The data were supported by QSAR study.
format Online
Article
Text
id pubmed-7866801
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-78668012021-02-07 Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents Redzicka, Aleksandra Czyżnikowska, Żaneta Wiatrak, Benita Gębczak, Katarzyna Kochel, Andrzej Int J Mol Sci Article In the present paper, we describe the biological activity of the newly designed and synthesized series N-substituted 3,4-pyrroledicarboximides 2a–2p. The compounds 2a–2p were obtained in good yields by one-pot, three-component condensation of pyrrolo[3,4-c]pyrrole scaffold (1a–c) with secondary amines and an excess of formaldehyde solution in C(2)H(5)OH. The structural properties of the compounds were characterized by (1)H NMR, (13)C NMR FT-IR, MS, and elemental analysis. Moreover, single crystal X-ray diffraction has been recorded for compound 2h. The colorimetric inhibitor screening assay was used to obtain their potencies to inhibit COX-1 and COX-2 enzymes. According to the results, all of the tested compounds inhibited the activity of COX-1 and COX-2. Theoretical modeling was also applied to describe the binding properties of compounds towards COX-1 and COX-2 cyclooxygenase isoform. The data were supported by QSAR study. MDPI 2021-01-30 /pmc/articles/PMC7866801/ /pubmed/33573356 http://dx.doi.org/10.3390/ijms22031410 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Redzicka, Aleksandra
Czyżnikowska, Żaneta
Wiatrak, Benita
Gębczak, Katarzyna
Kochel, Andrzej
Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title_full Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title_fullStr Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title_full_unstemmed Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title_short Design and Synthesis of N-Substituted 3,4-Pyrroledicarboximides as Potential Anti-Inflammatory Agents
title_sort design and synthesis of n-substituted 3,4-pyrroledicarboximides as potential anti-inflammatory agents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7866801/
https://www.ncbi.nlm.nih.gov/pubmed/33573356
http://dx.doi.org/10.3390/ijms22031410
work_keys_str_mv AT redzickaaleksandra designandsynthesisofnsubstituted34pyrroledicarboximidesaspotentialantiinflammatoryagents
AT czyznikowskazaneta designandsynthesisofnsubstituted34pyrroledicarboximidesaspotentialantiinflammatoryagents
AT wiatrakbenita designandsynthesisofnsubstituted34pyrroledicarboximidesaspotentialantiinflammatoryagents
AT gebczakkatarzyna designandsynthesisofnsubstituted34pyrroledicarboximidesaspotentialantiinflammatoryagents
AT kochelandrzej designandsynthesisofnsubstituted34pyrroledicarboximidesaspotentialantiinflammatoryagents