Synthesis, crystal structure and biological evaluation of new phosphoramide derivatives as urease inhibitors using docking, QSAR and kinetic studies.


Journal

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

Informations de publication

Date de publication:
05 2019
Historique:
received: 01 11 2018
revised: 20 01 2019
accepted: 27 01 2019
pubmed: 18 2 2019
medline: 14 4 2020
entrez: 18 2 2019
Statut: ppublish

Résumé

In an attempt to achieve a new class of phosphoramide inhibitors with high potency and resistance to the hydrolysis process against urease enzyme, we synthesized a series of bisphosphoramide derivatives (01-43) and characterized them by various spectroscopic techniques. The crystal structures of compounds 22 and 26 were investigated using X-ray crystallography. The inhibitory activities of the compounds were evaluated against the jack bean urease and were compared to monophosphoramide derivatives and other known standard inhibitors. The compounds containing aromatic amines and their substituted derivatives exhibited very high inhibitory activity in the range of IC

Identifiants

pubmed: 30772649
pii: S0045-2068(18)31251-3
doi: 10.1016/j.bioorg.2019.01.064
pii:
doi:

Substances chimiques

Enzyme Inhibitors 0
Phosphoramides 0
phosphoramide 13597-72-3
Urease EC 3.5.1.5

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

482-493

Informations de copyright

Crown Copyright © 2019. Published by Elsevier Inc. All rights reserved.

Auteurs

Khodayar Gholivand (K)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran. Electronic address: gholi_kh@modares.ac.ir.

Mahsa Pooyan (M)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran.

Fahimeh Mohammadpanah (F)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran.

Foroogh Pirastefar (F)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran.

Peter C Junk (PC)

College of Science & Engineering, James Cook University, Townsville, Queensland 4811, Australia.

Jun Wang (J)

College of Science & Engineering, James Cook University, Townsville, Queensland 4811, Australia.

Ali Asghar Ebrahimi Valmoozi (AA)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran.

Ahmad Mani-Varnosfaderani (A)

Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran.

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Classifications MeSH