Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic.

Cells, Cultured Drug Design Fibroblasts / drug effects Glycoside Hydrolase Inhibitors / chemical synthesis Humans Models, Molecular Molecular Docking Simulation Molecular Structure Protein Binding Protein Conformation Pyrans / chemical synthesis alpha-Glucosidases / metabolism
Docking study Pharmacokinetic prediction Quinazolinone-dihydropyrano[3,2-b]pyran hybrids Type 2 diabetes α-Amylase α-Glucosidase

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
04 2021
Historique:
received: 30 07 2020
revised: 29 12 2020
accepted: 28 01 2021
pubmed: 21 2 2021
medline: 1 10 2021
entrez: 20 2 2021
Statut: ppublish

Résumé

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC

Identifiants

DOI: 10.1016/j.bioorg.2021.104703 PMID: 33609917
pubmed: 33609917
pii: S0045-2068(21)00079-1
doi: 10.1016/j.bioorg.2021.104703
pii:
doi:

Substances chimiques

Glycoside Hydrolase Inhibitors 0
Pyrans 0
alpha-Glucosidases EC 3.2.1.20

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

104703

Informations de copyright

Copyright © 2021 Elsevier Inc. All rights reserved.

Auteurs

Maedeh Sherafati (M)

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran.

Roghieh Mirzazadeh (R)

Department of Biochemistry, Pasteur Institute of Iran, Tehran, Iran.

Ebrahim Barzegari (E)

Medical Biology Research Center, Health Technology Institute, Kermanshah University of Medical Sciences, Kermanshah, Iran.

Maryam Mohammadi-Khanaposhtani (M)

Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran.

Homa Azizian (H)

Department of Medicinal Chemistry, School of Pharmacy, Iran University of Medical Sciences, Tehran, Iran.

Mohammad Sadegh Asgari (M)

Department of Chemistry, Iran University of Science and Technology, Tehran, Iran.

Samanesadat Hosseini (S)

Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.

Ebrahim Zabihi (E)

Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran.

Somayeh Mojtabavi (S)

Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

Mohammad Ali Faramarzi (M)

Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

Mohammad Mahdavi (M)

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran. Electronic address: momahdavi@tums.ac.ir.

Bagher Larijani (B)

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran.

Hossein Rastegar (H)

Cosmetic Products Research Center, Iranian Food and Drug Administration, MOHE, Tehran, Iran.

Haleh Hamedifar (H)

CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran.

Mir Hamed Hajimiri (M)

Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, Iran. Electronic address: h.hajimiri@nanoalvand.com.

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Classifications MeSH

questionsmedicales.fr › Cellules › Cellules cultivées › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Techniques d'investigation › Développement de médicament › Découverte de médicament › Conception de médicament › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Cellules › Cellules du tissu conjonctif › Fibroblastes › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Hypoglycémiants › Inhibiteurs des glycoside hydrolases › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Métabolisme › Liaison aux protéines › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › Conformation des protéines › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Pyrannes › Quinazolinone-dihydropyrano[3,2-b]pyran...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Glycosidases › Glucosidases › alpha-Glucosidase › Quinazolinone-dihydropyrano[3,2-b]pyran...