Quinazoline and phthalazine derivatives as novel melatonin receptor ligands analogues of agomelatine

For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying...

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Published inEuropean journal of medicinal chemistry Vol. 189; p. 112078
Main Authors Bolteau, Raphaël, Descamps, Florian, Ettaoussi, Mohamed, Caignard, Daniel H., Delagrange, Philippe, Melnyk, Patricia, Yous, Saïd
Format Journal Article
LanguageEnglish
Published ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.03.2020
Elsevier
Subjects
Acetamides - chemistry
Acetamides - metabolism
Agomelatine
Agonist
Animals
Chemical Sciences
Chemistry, Medicinal
CHO Cells
Cricetinae
Cricetulus
HEK293 Cells
Humans
Life Sciences & Biomedicine
Ligands
Melatonin receptor
MT1
MT2
Pharmacology & Pharmacy
Phthalazine
Phthalazines - chemistry
Phthalazines - metabolism
Quinazoline
Quinazolines - chemistry
Quinazolines - metabolism
Receptor, Melatonin, MT1 - metabolism
Receptor, Melatonin, MT2 - metabolism
Science & Technology
Structure-Activity Relationship
Agonist
Phthalazine
MLT
AGM
Agomelatine
MT2
MT1
Quinazoline
Melatonin receptor
DESIGN
SERIES
MT1/MT2
RAMELTEON
PHARMACOLOGICAL EVALUATION
MT
Online AccessGet full text

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Abstract For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties. [Display omitted] •New quinazoline and phthalazine analogues of agomelatine were prepared•Obtained compounds showed good melatonergic affinity and no 5-HT2C affinity•Quinazoline 11c showed the most interesting results of this series•Phthalazine 20c showed a10 times MT2-selectivity over MT1
AbstractList For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT and MT ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT and MT , in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties.
For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties. (C) 2020 Elsevier Masson SAS. All rights reserved.
For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties.
For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and pharmacological results of a new family of melatonin receptor ligands. Issued from the introduction of quinazoline and phthalazine scaffolds carrying an ethyl amide lateral chain and a methoxy group as bioisosteric ligands analogues of previously developed Agomelatine. The biological activity of the prepared analogues was compared with that of Agomelatine. Quinazoline and phthalazine rings proved to be a versatile scaffold for easy feasible MT1 and MT2 ligands. Potent agonists with sub-micromolar binding affinity were obtained. However, the presence of two nitrogen atoms resulted in compounds with lower affinity for both MT1 and MT2, in comparison with the parent compound, balanced by the exhibition of good pharmacokinetic properties. [Display omitted] •New quinazoline and phthalazine analogues of agomelatine were prepared•Obtained compounds showed good melatonergic affinity and no 5-HT2C affinity•Quinazoline 11c showed the most interesting results of this series•Phthalazine 20c showed a10 times MT2-selectivity over MT1
ArticleNumber 112078
Author Yous, Saïd
Caignard, Daniel H.
Ettaoussi, Mohamed
Bolteau, Raphaël
Descamps, Florian
Delagrange, Philippe
Melnyk, Patricia
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Keywords Agonist
Phthalazine
MLT
AGM
Agomelatine
MT2
MT1
Quinazoline
Melatonin receptor
DESIGN
SERIES
MT1/MT2
RAMELTEON
PHARMACOLOGICAL EVALUATION
MT
Language English
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Snippet For further development of successors of Agomelatine through modulation of its pharmacokinetic properties, we report herein the design, synthesis and...
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SubjectTerms Acetamides - chemistry
Acetamides - metabolism
Agomelatine
Agonist
Animals
Chemical Sciences
Chemistry, Medicinal
CHO Cells
Cricetinae
Cricetulus
HEK293 Cells
Humans
Life Sciences & Biomedicine
Ligands
Melatonin receptor
MT1
MT2
Pharmacology & Pharmacy
Phthalazine
Phthalazines - chemistry
Phthalazines - metabolism
Quinazoline
Quinazolines - chemistry
Quinazolines - metabolism
Receptor, Melatonin, MT1 - metabolism
Receptor, Melatonin, MT2 - metabolism
Science & Technology
Structure-Activity Relationship
Title Quinazoline and phthalazine derivatives as novel melatonin receptor ligands analogues of agomelatine
URI https://dx.doi.org/10.1016/j.ejmech.2020.112078
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https://www.ncbi.nlm.nih.gov/pubmed/32004937
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Volume 189
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