Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands

Pégurier, Cécile; Morellato, Laurence; Chahed, Eminn; Andrieux, Jean; Nicolas, Jean Paul; Boutin, Jean A.; Bennejean, Caroline; Delagrange, Philippe; Langlois, Michel; Mathé-Allainmat, Monique

doi:10.1016/s0968-0896(02)00328-0

Cited by 13 publications

(10 citation statements)

References 25 publications

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“…Indanyl piperazine derivatives have also been prepared from 12b (R = OMe) [76]. The phenyl ring is a sufficient core to provide compounds with significant potency as melatonin agonists [77][78][79][80][81]. The methoxyl and amide substituents have to be the appropriate distance apart.…”

Section: Indole Benzo[b]thiophene Benzo[b]furan Benzimidazoles Inmentioning

confidence: 99%

Synthesis of Compounds as Melatonin Agonists and Antagonists

Garratt¹,

Tsotinis

2007

MRMC

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The functions of melatonin, the hormone of the pineal gland, are of considerable current interest. Synthetic melatonin analogues as agonists and antagonists have been explored in some detail and the molecule can be considered as consisting of an indole core, acting mainly as a spacer, and the 5-methoxyl and 3-amidoethyl side chains acting as the functional components, as originally proposed by Heward and Hadley. This review focuses on the synthetic routes to these melatonin analogues, first of the core, then of the substituents that have been attached to the core, and finally those compounds with restricted conformations and those that are chiral. The importance of the various factors involved in the activity of the compounds as agonist or antagonists is indicated, as is the difference in activity of enantiomers.

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Section: Indole Benzo[b]thiophene Benzo[b]furan Benzimidazoles Inmentioning

confidence: 99%

Synthesis of Compounds as Melatonin Agonists and Antagonists

Garratt¹,

Tsotinis

2007

MRMC

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“…One method enabled rapid analogue production of the tropane portion of 1 by reaction of a biaryl oxylamine with an appropriate ketone. The biaryl oxylamine was synthesised via deprotection of the corresponding benzhydryloxyphthalimide 6 which in turn was synthesised from the biaryl alcohol, either directly through a Mitsunobu reaction 6 or via its corresponding chloride. 7,8 The second method enabled rapid analogue production of the benzhydryl portion, through reaction of the tropinone oxime with an appropriate arylmethyl chloride.…”

mentioning

confidence: 99%

Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi

Holloway

Parisot

Novello

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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“…Almost all the scaffolds shown in Figure 2 were bearing at least one of these features, with rare exceptions. The ethylamide moiety was either included in a cycle, 33,43,87,94,106,118,122 or bearing a double bond 87,94 or various substituents, such as CF 3 , 45,109,110,120 CHF 2 , 45,132 CH 2 Cl, 34,117 a cyclopropyl moiety 29,102,114,116,133 or a cyclobutyl moiety 42,66 to name only a few.…”

Section: The Alkoxy and N‐acylamino Decorationsmentioning

confidence: 99%

Melatonin receptor ligands: A pharmaco‐chemical perspective

Boutin

Witt‐Enderby

Sotriffer

et al. 2020

Journal of Pineal Research

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Melatonin MT1 and MT2 receptor ligands have been vigorously explored for the last 4 decades. Inspection of approximately 80 publications in the field revealed that most melatonergic ligands were structural analogues of melatonin combining three essential features of the parent compound: an aromatic ring bearing a methoxy group and an amide side chain in a relative arrangement similar to that present in melatonin. While several series of MT2‐selective agents—agonists, antagonists, or partial agonists—were reported, the field was lacking MT1‐selective agents. Herein, we describe various approaches toward the development of melatonergic ligands, keeping in mind that most of the molecules/pharmacophores obtained were essentially melatonin copies, even though diverse tri‐ or tetra‐cyclic compounds were explored. In addition to lack of structural diversity, only few studies examined the activity of the reported melatonergic ligands in vivo. Moreover, an extensive pharmacological characterization including biopharmaceutical stability, pharmacokinetic properties, specificity toward other major receptors to name a few remained scarce. For example, many of the antagonists described were not stable in vivo, were not selective for the melatonin receptor subtype of interest, and were not fully characterized from a pharmacological standpoint. Indeed, virtual screening of large compound libraries has led to the recent discovery of potent and selective melatonin receptor agonists and partial agonists of new chemotypes. Having said this, the melatonergic field is still lacking subtype‐selective melatonin receptor antagonists “active” in vivo, which are critical to our understanding of melatonin and melatonin receptors’ role in basic physiology and disease.

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Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands

Cited by 13 publications

References 25 publications

Synthesis of Compounds as Melatonin Agonists and Antagonists

Synthesis of Compounds as Melatonin Agonists and Antagonists

Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi

Melatonin receptor ligands: A pharmaco‐chemical perspective

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