Synthesis and SAR Studies of Isoquinoline and Tetrahydroisoquinoline Derivatives as Melatonin Receptor Ligands

In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of...

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Published inChemMedChem Vol. 17; no. 3; pp. e202100658 - n/a
Main Authors Ettaoussi, Mohamed, Laversin, Amélie, Vreulz, Brandon, Rami, Marouane, Lebegue, Nicolas, Delagrange, Philippe, Caignard, Daniel Henri, Melnyk, Patricia, Liberelle, Maxime, Yous, Saïd
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 04.02.2022
Wiley Subscription Services, Inc
Subjects
Affinity
agomelatine
Agonists
Animals
Binding
Cells, Cultured
Chemical Sciences
Chemistry, Medicinal
Cricetulus
Dose-Response Relationship, Drug
Humans
isoquinoline
Isoquinolines - chemistry
Isoquinolines - metabolism
Isoquinolines - pharmacology
Life Sciences
Life Sciences & Biomedicine
Ligands
Melatonin
Molecular Docking Simulation
Molecular Structure
MT1/MT2
Naphthalene
Nitrogen
Pharmacokinetics
Pharmacology
Pharmacology & Pharmacy
Receptors, Melatonin - agonists
Science & Technology
Serotonin S2 receptors
Structure-Activity Relationship
Tetrahydroisoquinoline
DESIGN
POTENT
ACID
isoquinoline
ANALOGS
tetrahydroisoquinoline
MT1/MT2
MT2
MT1
agomelatine
melatonin
DISCOVERY
Online AccessGet full text

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Abstract In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT1 and MT2 and the loss of 5HT2C response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds. Successors of agomelatine: A series of isoquinoline and tetrahydroisoquinoline derivatives were shown to have good melatonergic affinity and no 5‐HT2C affinity. Compounds 38 and 43 demonstrated the most interesting binding affinities, whereas tetrahydroisoquinoline 23 showed 45‐fold MT2 selectivity over the MT1 receptor subtype.
AbstractList Supporting information for this article is given via a link at the end of the document.
In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT1 and MT2 and the loss of 5HT2C response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds.
Abstract In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT 1 and MT 2 and the loss of 5HT 2C response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds.
In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT and MT and the loss of 5HT response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds.
In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT1 and MT2 and the loss of 5HT(2C) response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds.
In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene ring. The isoquinoline and tetrahydroisoquinoline derivatives were synthesized and pharmacologically evaluated. This isosteric replacement of the naphthalene group of agomelatine has led to potent agonist and partial agonist compounds with nanomolar melatonergic binding affinities. Overall, the presence of a nitrogen atom was accompanied with a decrease in the binding affinity toward both MT1 and MT2 and the loss of 5HT2C response, especially for tetrahydroisoquinoline in comparison with the parent compound. Interestingly, due to the presence of this nitrogen atom, a notable improvement in the pharmacokinetic properties was observed for all compounds. Successors of agomelatine: A series of isoquinoline and tetrahydroisoquinoline derivatives were shown to have good melatonergic affinity and no 5‐HT2C affinity. Compounds 38 and 43 demonstrated the most interesting binding affinities, whereas tetrahydroisoquinoline 23 showed 45‐fold MT2 selectivity over the MT1 receptor subtype.
Author Yous, Saïd
Ettaoussi, Mohamed
Rami, Marouane
Vreulz, Brandon
Caignard, Daniel Henri
Liberelle, Maxime
Delagrange, Philippe
Laversin, Amélie
Lebegue, Nicolas
Melnyk, Patricia
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Issue 3
Keywords DESIGN
POTENT
ACID
isoquinoline
ANALOGS
tetrahydroisoquinoline
MT1/MT2
MT2
MT1
agomelatine
melatonin
DISCOVERY
Language English
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e_1_2_7_63_1
e_1_2_7_12_2
e_1_2_7_42_2
e_1_2_7_65_1
e_1_2_7_10_2
e_1_2_7_44_2
e_1_2_7_67_2
Frackenpohl J. (e_1_2_7_4_2) 2000
e_1_2_7_10_1
e_1_2_7_46_2
e_1_2_7_69_1
e_1_2_7_48_2
e_1_2_7_27_2
Adams R. (e_1_2_7_52_1) 1969
e_1_2_7_51_1
e_1_2_7_70_1
e_1_2_7_30_1
e_1_2_7_24_2
e_1_2_7_32_1
e_1_2_7_55_1
e_1_2_7_22_1
e_1_2_7_34_1
e_1_2_7_57_1
e_1_2_7_20_2
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e_1_2_7_59_1
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SSID ssj0044818
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Snippet In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the naphthalene...
Abstract In our constant search for new successors of agomelatine, we report herein a new series of compounds resulting from bioisosteric modulation of the...
Supporting information for this article is given via a link at the end of the document.
Source Web of Science
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pubmed
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wiley
SourceType Open Access Repository
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StartPage e202100658
SubjectTerms Affinity
agomelatine
Agonists
Animals
Binding
Cells, Cultured
Chemical Sciences
Chemistry, Medicinal
Cricetulus
Dose-Response Relationship, Drug
Humans
isoquinoline
Isoquinolines - chemistry
Isoquinolines - metabolism
Isoquinolines - pharmacology
Life Sciences
Life Sciences & Biomedicine
Ligands
Melatonin
Molecular Docking Simulation
Molecular Structure
MT1/MT2
Naphthalene
Nitrogen
Pharmacokinetics
Pharmacology
Pharmacology & Pharmacy
Receptors, Melatonin - agonists
Science & Technology
Serotonin S2 receptors
Structure-Activity Relationship
Tetrahydroisoquinoline
Title Synthesis and SAR Studies of Isoquinoline and Tetrahydroisoquinoline Derivatives as Melatonin Receptor Ligands
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcmdc.202100658
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000724233900001
https://www.ncbi.nlm.nih.gov/pubmed/34797951
https://www.proquest.com/docview/2625204428/abstract/
https://search.proquest.com/docview/2600287032
https://hal.science/hal-04338506
Volume 17
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