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New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment

This paper reports the synthesis, analgesic activity, acute toxicity and histopathological (HP) assessment of four new compounds from oxazol-5(4H)-ones class that contain in their molecule a diarylsulfone moiety. The new 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones were obtained...

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Autores principales: Bărbuceanu, Florica, Roşca, Elena-Valentina, Apostol, Theodora-Venera, Şeremet, Oana-Cristina, Drăghici, Constantin, Mihai, Dragoş Paul, Negreş, Simona, Niţulescu, George Mihai, Bărbuceanu, Ştefania-Felicia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Academy of Medical Sciences, Romanian Academy Publishing House, Bucharest 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7864298/
https://www.ncbi.nlm.nih.gov/pubmed/33544801
http://dx.doi.org/10.47162/RJME.61.2.19
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author Bărbuceanu, Florica
Roşca, Elena-Valentina
Apostol, Theodora-Venera
Şeremet, Oana-Cristina
Drăghici, Constantin
Mihai, Dragoş Paul
Negreş, Simona
Niţulescu, George Mihai
Bărbuceanu, Ştefania-Felicia
author_facet Bărbuceanu, Florica
Roşca, Elena-Valentina
Apostol, Theodora-Venera
Şeremet, Oana-Cristina
Drăghici, Constantin
Mihai, Dragoş Paul
Negreş, Simona
Niţulescu, George Mihai
Bărbuceanu, Ştefania-Felicia
author_sort Bărbuceanu, Florica
collection PubMed
description This paper reports the synthesis, analgesic activity, acute toxicity and histopathological (HP) assessment of four new compounds from oxazol-5(4H)-ones class that contain in their molecule a diarylsulfone moiety. The new 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones were obtained by reaction of 2-(4-(4-bromophenyl-sulfonyl)benzamido)acetic acid intermediate with aromatic aldehydes (benzaldehyde, 4-methoxy, 4-nitro or 4-bromobenzaldehyde), in acetic anhydride and in the presence of anhydrous sodium acetate. The new compounds have been characterized by spectral techniques, such as: Fourier-transform infrared spectroscopy (FT-IR), mass spectrometry (MS), proton nuclear magnetic resonance ((1)H-NMR) and by elemental analysis. The acute toxicity of the new oxazol-5(4H)-ones in mice was assessed through “acute toxic class” method, according to Organization for Economic Co-operation and Development (OECD) Guidelines. The HP assessment of some preserved organs collected from mice has been performed. The analgesic activity of all new synthesized compounds was carried out with two pharmacological tests: the writhing test and the hot plate test. In order to predict the binding affinities of the synthesized oxazol-5(4H)-ones derivatives against molecular targets involved in pain and inflammation, molecular docking simulations were performed. The results of the writhing test indicated that the most active compound was the oxazolone that contains in the molecule a methoxy group. The acute oral toxicity study revealed no lethal effect of new compounds. The HP assessment of the preserved organs collected from mice did not indicate any cytohistopathological aspects that can be linked to any inflammatory, neoplastic or cytotoxic process, demonstrating the low toxicity of new compounds.
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spelling pubmed-78642982021-02-08 New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment Bărbuceanu, Florica Roşca, Elena-Valentina Apostol, Theodora-Venera Şeremet, Oana-Cristina Drăghici, Constantin Mihai, Dragoş Paul Negreş, Simona Niţulescu, George Mihai Bărbuceanu, Ştefania-Felicia Rom J Morphol Embryol Original Paper This paper reports the synthesis, analgesic activity, acute toxicity and histopathological (HP) assessment of four new compounds from oxazol-5(4H)-ones class that contain in their molecule a diarylsulfone moiety. The new 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones were obtained by reaction of 2-(4-(4-bromophenyl-sulfonyl)benzamido)acetic acid intermediate with aromatic aldehydes (benzaldehyde, 4-methoxy, 4-nitro or 4-bromobenzaldehyde), in acetic anhydride and in the presence of anhydrous sodium acetate. The new compounds have been characterized by spectral techniques, such as: Fourier-transform infrared spectroscopy (FT-IR), mass spectrometry (MS), proton nuclear magnetic resonance ((1)H-NMR) and by elemental analysis. The acute toxicity of the new oxazol-5(4H)-ones in mice was assessed through “acute toxic class” method, according to Organization for Economic Co-operation and Development (OECD) Guidelines. The HP assessment of some preserved organs collected from mice has been performed. The analgesic activity of all new synthesized compounds was carried out with two pharmacological tests: the writhing test and the hot plate test. In order to predict the binding affinities of the synthesized oxazol-5(4H)-ones derivatives against molecular targets involved in pain and inflammation, molecular docking simulations were performed. The results of the writhing test indicated that the most active compound was the oxazolone that contains in the molecule a methoxy group. The acute oral toxicity study revealed no lethal effect of new compounds. The HP assessment of the preserved organs collected from mice did not indicate any cytohistopathological aspects that can be linked to any inflammatory, neoplastic or cytotoxic process, demonstrating the low toxicity of new compounds. Academy of Medical Sciences, Romanian Academy Publishing House, Bucharest 2020 2020-09-21 /pmc/articles/PMC7864298/ /pubmed/33544801 http://dx.doi.org/10.47162/RJME.61.2.19 Text en Copyright © 2020, Academy of Medical Sciences, Romanian Academy Publishing House, Bucharest http://creativecommons.org/licenses/by-nc-sa/4.0/ This is an open-access article distributed under the terms of a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International Public License, which permits unrestricted use, adaptation, distribution and reproduction in any medium, non-commercially, provided the new creations are licensed under identical terms as the original work and the original work is properly cited.
spellingShingle Original Paper
Bărbuceanu, Florica
Roşca, Elena-Valentina
Apostol, Theodora-Venera
Şeremet, Oana-Cristina
Drăghici, Constantin
Mihai, Dragoş Paul
Negreş, Simona
Niţulescu, George Mihai
Bărbuceanu, Ştefania-Felicia
New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title_full New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title_fullStr New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title_full_unstemmed New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title_short New 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4H)-ones: analgesic activity and histopathological assessment
title_sort new 2-(4-(4-bromophenylsulfonyl)phenyl)-4-arylidene-oxazol-5(4h)-ones: analgesic activity and histopathological assessment
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7864298/
https://www.ncbi.nlm.nih.gov/pubmed/33544801
http://dx.doi.org/10.47162/RJME.61.2.19
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