Synthesis, in vitro evaluation and molecular docking of a new class of indolylpropyl benzamidopiperazines as dual AChE and SERT ligands for Alzheimer's disease.


Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
15 Jul 2020
Historique:
received: 13 01 2020
revised: 11 04 2020
accepted: 20 04 2020
pubmed: 11 5 2020
medline: 27 1 2021
entrez: 11 5 2020
Statut: ppublish

Résumé

During the last decade, the one drug-one target strategy has resulted to be inefficient in facing diseases with complex ethiology like Alzheimer's disease and many others. In this context, the multitarget paradigm has emerged as a promising strategy. Based on this consideration, we aim to develop novel molecules as promiscuous ligands acting in two or more targets at the same time. For such purpose, a new series of indolylpropyl-piperazinyl oxoethyl-benzamido piperazines were synthesized and evaluated as multitarget-directed drugs for the serotonin transporter (SERT) and acetylcholinesterase (AChE). The ability to decrease β-amyloid levels as well as cell toxicity of all compounds were also measured. In vitro results showed that at least four compounds displayed promising activity against SERT and AChE. Compounds 18 and 19 (IC

Identifiants

pubmed: 32388114
pii: S0223-5234(20)30338-X
doi: 10.1016/j.ejmech.2020.112368
pii:
doi:

Substances chimiques

Amyloid beta-Peptides 0
Antidepressive Agents 0
Cholinesterase Inhibitors 0
Piperazines 0
Serotonin Plasma Membrane Transport Proteins 0
Serotonin Uptake Inhibitors 0
Donepezil 8SSC91326P
Acetylcholinesterase EC 3.1.1.7

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

112368

Informations de copyright

Copyright © 2020 Elsevier Masson SAS. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Julio Rodríguez-Lavado (J)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Carlos Gallardo-Garrido (C)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Michael Mallea (M)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Victor Bustos (V)

Laboratory of Cellular and Molecular Neuroscience, The Rockefeller University, New York, USA.

Rodrigo Osorio (R)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Martín Hödar-Salazar (M)

Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería Ciencias, Universidad de la Frontera, Temuco, Chile.

Hery Chung (H)

Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago, Chile.

Ramiro Araya-Maturana (R)

Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, Chile.

Marcos Lorca (M)

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares, Universidade de Santiago de Compostela, Santiago de Compostela, Spain; Instituto de Química y Bioquímica, Facultad de Ciencias, Universidad de Valparaíso, Valparaíso, Chile.

C David Pessoa-Mahana (CD)

Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago, Chile.

Jaime Mella-Raipán (J)

Instituto de Química y Bioquímica, Facultad de Ciencias, Universidad de Valparaíso, Valparaíso, Chile; Centro de Investigación Farmacopea Chilena (CIFAR), Universidad de Valparaíso, Santa Marta, Valparaíso, Chile.

Claudio Saitz (C)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Pablo Jaque (P)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile.

Miguel Reyes-Parada (M)

Centro de Investigación Biomédica y Aplicada (CIBAP), Escuela de Medicina, Facultad de Ciencias Médicas, Universidad de Santiago de Chile, Chile; Facultad de Ciencias de la Salud, Universidad Autónoma de Chile, Santiago, Chile.

Patricio Iturriaga-Vásquez (P)

Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería Ciencias, Universidad de la Frontera, Temuco, Chile; Center of Excellence in Biotechnology Research Applied to the Environment, Universidad de La Frontera, Temuco, Chile. Electronic address: patricio.iturriaga@ufrontera.cl.

Hernán Pessoa-Mahana (H)

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Olivos, 1007, Santiago, Chile. Electronic address: hpessoa@ciq.uchile.cl.

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Classifications MeSH