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Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines

[Image: see text] A series of new quinazoline derivatives were designed and synthesized via a one-pot condensation reaction between isatoic anhydride and aromatic aldehydes with anilines using aluminum sulfate as a catalyst in refluxing ethanol. Their structures were confirmed by their physical, IR,...

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Autores principales: Barmak, Alireza, Niknam, Khodabakhsh, Mohebbi, Gholamhossein
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6843711/
https://www.ncbi.nlm.nih.gov/pubmed/31720511
http://dx.doi.org/10.1021/acsomega.9b01906
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author Barmak, Alireza
Niknam, Khodabakhsh
Mohebbi, Gholamhossein
author_facet Barmak, Alireza
Niknam, Khodabakhsh
Mohebbi, Gholamhossein
author_sort Barmak, Alireza
collection PubMed
description [Image: see text] A series of new quinazoline derivatives were designed and synthesized via a one-pot condensation reaction between isatoic anhydride and aromatic aldehydes with anilines using aluminum sulfate as a catalyst in refluxing ethanol. Their structures were confirmed by their physical, IR, (1)H NMR, (13)C NMR, and mass spectroscopy data and evaluated for some biological effects, including the antioxidant and α-glucosidase inhibitory activities as well as some in vivo hematological parameters. The ability of synthesized compounds in the inhibition of α-glucosidase was also investigated through the in silico study. The significant and important changes in some hematological tests were perceived. Notably, compound 4h showed more reducing effects on cholesterol and triglyceride levels. This molecule certainly has the potential to be developed as the antihyperlipemic compound. The tested compounds, in particular, compounds 4j and 4l, were found to be uniquely reducing blood sugar levels. The entire synthesized compounds showed the potent α-glucosidase inhibitory activity compared with acarbose as a standard material. Amongst, the compounds 4h and 4i showed the strongest enzyme inhibitory potentials than the standard drug acarbose. There was a good correlation between in vitro and in silico studies for ligands 4i and 4l. The majority of compounds presented a good radical scavenging activity, though the compound 4j exhibited the strongest activity, even to the standard of ascorbic acid. Further studies are required to determine whether these main compounds could be a potential treatment for diabetes and hyperlipidemia diseases.
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spelling pubmed-68437112019-11-12 Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines Barmak, Alireza Niknam, Khodabakhsh Mohebbi, Gholamhossein ACS Omega [Image: see text] A series of new quinazoline derivatives were designed and synthesized via a one-pot condensation reaction between isatoic anhydride and aromatic aldehydes with anilines using aluminum sulfate as a catalyst in refluxing ethanol. Their structures were confirmed by their physical, IR, (1)H NMR, (13)C NMR, and mass spectroscopy data and evaluated for some biological effects, including the antioxidant and α-glucosidase inhibitory activities as well as some in vivo hematological parameters. The ability of synthesized compounds in the inhibition of α-glucosidase was also investigated through the in silico study. The significant and important changes in some hematological tests were perceived. Notably, compound 4h showed more reducing effects on cholesterol and triglyceride levels. This molecule certainly has the potential to be developed as the antihyperlipemic compound. The tested compounds, in particular, compounds 4j and 4l, were found to be uniquely reducing blood sugar levels. The entire synthesized compounds showed the potent α-glucosidase inhibitory activity compared with acarbose as a standard material. Amongst, the compounds 4h and 4i showed the strongest enzyme inhibitory potentials than the standard drug acarbose. There was a good correlation between in vitro and in silico studies for ligands 4i and 4l. The majority of compounds presented a good radical scavenging activity, though the compound 4j exhibited the strongest activity, even to the standard of ascorbic acid. Further studies are required to determine whether these main compounds could be a potential treatment for diabetes and hyperlipidemia diseases. American Chemical Society 2019-10-25 /pmc/articles/PMC6843711/ /pubmed/31720511 http://dx.doi.org/10.1021/acsomega.9b01906 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Barmak, Alireza
Niknam, Khodabakhsh
Mohebbi, Gholamhossein
Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title_full Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title_fullStr Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title_full_unstemmed Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title_short Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines
title_sort synthesis, structural studies, and α-glucosidase inhibitory, antidiabetic, and antioxidant activities of 2,3-dihydroquinazolin-4(1h)-ones derived from pyrazol-4-carbaldehyde and anilines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6843711/
https://www.ncbi.nlm.nih.gov/pubmed/31720511
http://dx.doi.org/10.1021/acsomega.9b01906
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