Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives

A new series of N'-substituted benzylidene-2-(4-oxo-2-phenyl-1,4-dihydroquinazolin-3(2H)-yl)acetohydrazide (5a–5h) has been synthesized, characterized by FT-IR, NMR spectroscopy and mass spectrometry and tested against human monoamine oxidase (MAO) A and B. Only (4-hydroxy-3-methoxybenzylidene)...

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Autores principales: Amer, Adel, Hegazi, Abdelrahman H., Alshekh, Mohammed Khalil, Ahmed, Hany E. A., Soliman, Saied M., Maniquet, Antonin, Ramsay, Rona R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7211837/
https://www.ncbi.nlm.nih.gov/pubmed/32431898
http://dx.doi.org/10.1098/rsos.200050
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author Amer, Adel
Hegazi, Abdelrahman H.
Alshekh, Mohammed Khalil
Ahmed, Hany E. A.
Soliman, Saied M.
Maniquet, Antonin
Ramsay, Rona R.
author_facet Amer, Adel
Hegazi, Abdelrahman H.
Alshekh, Mohammed Khalil
Ahmed, Hany E. A.
Soliman, Saied M.
Maniquet, Antonin
Ramsay, Rona R.
author_sort Amer, Adel
collection PubMed
description A new series of N'-substituted benzylidene-2-(4-oxo-2-phenyl-1,4-dihydroquinazolin-3(2H)-yl)acetohydrazide (5a–5h) has been synthesized, characterized by FT-IR, NMR spectroscopy and mass spectrometry and tested against human monoamine oxidase (MAO) A and B. Only (4-hydroxy-3-methoxybenzylidene) substituted compounds gave submicromolar inhibition of MAO-A and MAO-B. Changing the phenyl substituent to methyl on the unsaturated quinazoline ring (12a–12d) decreased inhibition, but a less flexible linker (14a–14d) resulted in selective micromolar inhibition of hMAO-B providing insight for ongoing design. [Image: see text]
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spelling pubmed-72118372020-05-19 Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives Amer, Adel Hegazi, Abdelrahman H. Alshekh, Mohammed Khalil Ahmed, Hany E. A. Soliman, Saied M. Maniquet, Antonin Ramsay, Rona R. R Soc Open Sci Chemistry A new series of N'-substituted benzylidene-2-(4-oxo-2-phenyl-1,4-dihydroquinazolin-3(2H)-yl)acetohydrazide (5a–5h) has been synthesized, characterized by FT-IR, NMR spectroscopy and mass spectrometry and tested against human monoamine oxidase (MAO) A and B. Only (4-hydroxy-3-methoxybenzylidene) substituted compounds gave submicromolar inhibition of MAO-A and MAO-B. Changing the phenyl substituent to methyl on the unsaturated quinazoline ring (12a–12d) decreased inhibition, but a less flexible linker (14a–14d) resulted in selective micromolar inhibition of hMAO-B providing insight for ongoing design. [Image: see text] The Royal Society 2020-04-22 /pmc/articles/PMC7211837/ /pubmed/32431898 http://dx.doi.org/10.1098/rsos.200050 Text en © 2020 The Authors. http://creativecommons.org/licenses/by/4.0/ http://creativecommons.org/licenses/by/4.0/http://creativecommons.org/licenses/by/4.0/Published by the Royal Society under the terms of the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/, which permits unrestricted use, provided the original author and source are credited.
spellingShingle Chemistry
Amer, Adel
Hegazi, Abdelrahman H.
Alshekh, Mohammed Khalil
Ahmed, Hany E. A.
Soliman, Saied M.
Maniquet, Antonin
Ramsay, Rona R.
Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title_full Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title_fullStr Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title_full_unstemmed Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title_short Design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
title_sort design, synthesis, molecular modelling and in vitro screening of monoamine oxidase inhibitory activities of novel quinazolyl hydrazine derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7211837/
https://www.ncbi.nlm.nih.gov/pubmed/32431898
http://dx.doi.org/10.1098/rsos.200050
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