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Medchemcomm
2019 Mar 01;103:460-464. doi: 10.1039/c8md00604k.
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Fluorine substituted methoxyphenylalkyl amides as potent melatonin receptor agonists.
Tsotinis A
,
Kompogennitaki R
,
Papanastasiou I
,
Garratt PJ
,
Bocianowska A
,
Sugden D
.
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A series of fluorine substituted methoxyphenylalkyl amides were prepared with different orientations of the fluorine and methoxy groups with respect to the alkylamide side chain and with alkyl sides of differing lengths (n = 1-3). β-Dimethyl and α-methyl derivatives were also synthesised. The compounds were tested as melatonin agonists and antagonists using the pigment aggregation of Xenopus melanophores as the biological assay. A number of these compounds were potent melatonin agonists, the potency depending on the length of the alkyl chain, the orientation of the methoxy and fluorine substituents, the amide chain length and, for the ethyl side-chain analogues, the presence of β-substituents.
Arendt,
Managing jet lag: Some of the problems and possible new solutions.
2009, Pubmed
Arendt,
Managing jet lag: Some of the problems and possible new solutions.
2009,
Pubmed
Beyer,
Antioxidant properties of melatonin--an emerging mystery.
1998,
Pubmed
Blair,
Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines.
2000,
Pubmed
Blask,
Melatonin, sleep disturbance and cancer risk.
2009,
Pubmed
Boutin,
[Melatonin binding site MT3 is QR2: state of the art].
2007,
Pubmed
Brzezinski,
Effects of exogenous melatonin on sleep: a meta-analysis.
2005,
Pubmed
Carocci,
Design, synthesis, and pharmacological effects of structurally simple ligands for MT(1) and MT(2) melatonin receptors.
2010,
Pubmed
Cassone,
Melatonin's role in vertebrate circadian rhythms.
1998,
Pubmed
Cecon,
Melatonin receptors: molecular pharmacology and signalling in the context of system bias.
2018,
Pubmed
Descamps,
Influence of the novel antidepressant and melatonin agonist/serotonin2C receptor antagonist, agomelatine, on the rat sleep-wake cycle architecture.
2009,
Pubmed
Emens,
Diagnosis and Treatment of Non-24-h Sleep-Wake Disorder in the Blind.
2017,
Pubmed
Faust,
Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles.
2000,
Pubmed
,
Xenbase
Feng,
Early melatonin supplementation alleviates oxidative stress in a transgenic mouse model of Alzheimer's disease.
2006,
Pubmed
Fowler,
Melatonin does not "directly scavenge hydrogen peroxide": demise of another myth.
2003,
Pubmed
Garratt,
Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkyl amides.
1996,
Pubmed
Grant,
Melatonin and breast cancer: cellular mechanisms, clinical studies and future perspectives.
2009,
Pubmed
Hack,
The effects of low-dose 0.5-mg melatonin on the free-running circadian rhythms of blind subjects.
2003,
Pubmed
He,
The nuclear melatonin receptor RORα is a novel endogenous defender against myocardial ischemia/reperfusion injury.
2016,
Pubmed
Hu,
Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands.
2010,
Pubmed
Jockers,
Update on melatonin receptors: IUPHAR Review 20.
2016,
Pubmed
Kamel,
Insomnia in the elderly: cause, approach, and treatment.
2006,
Pubmed
Korkmaz,
Melatonin: an established antioxidant worthy of use in clinical trials.
2009,
Pubmed
Lewy,
The phase shift hypothesis for the circadian component of winter depression.
2007,
Pubmed
Mahlberg,
Normative data on the daily profile of urinary 6-sulfatoxymelatonin in healthy subjects between the ages of 20 and 84.
2006,
Pubmed
Olcese,
Protection against cognitive deficits and markers of neurodegeneration by long-term oral administration of melatonin in a transgenic model of Alzheimer disease.
2009,
Pubmed
Pappolla,
An assessment of the antioxidant and the antiamyloidogenic properties of melatonin: implications for Alzheimer's disease.
2000,
Pubmed
Reiter,
The melatonin rhythm: both a clock and a calendar.
1993,
Pubmed
Scheer,
Melatonin, sleep, and circadian rhythms.
2005,
Pubmed
Sharma,
Physiological neuroprotection by melatonin in a 6-hydroxydopamine model of Parkinson's disease.
2006,
Pubmed
Skene,
Human circadian rhythms: physiological and therapeutic relevance of light and melatonin.
2006,
Pubmed
Slominski,
Melatonin in the skin: synthesis, metabolism and functions.
2008,
Pubmed
Srinivasan,
Jet lag: therapeutic use of melatonin and possible application of melatonin analogs.
2008,
Pubmed
Sugden,
Design of subtype selective melatonin receptor agonists and antagonists.
1999,
Pubmed
,
Xenbase
Tsotinis,
Mapping the melatonin receptor. 7. Subtype selective ligands based on beta-substituted N-acyl-5-methoxytryptamines and beta-substituted N-acyl-5-methoxy-1-methyltryptamines.
2006,
Pubmed
,
Xenbase
Wade,
Efficacy of prolonged release melatonin in insomnia patients aged 55-80 years: quality of sleep and next-day alertness outcomes.
2007,
Pubmed
Wurtman,
Ramelteon: a novel treatment for the treatment of insomnia.
2006,
Pubmed
Zammit,
Evaluation of the efficacy and safety of ramelteon in subjects with chronic insomnia.
2007,
Pubmed
Zhu,
3-Methoxylphenylpropyl amides as novel receptor subtype-selective melatoninergic ligands: characterization of physicochemical and pharmacokinetic properties.
2011,
Pubmed
Zlotos,
MT1 and MT2 melatonin receptors: ligands, models, oligomers, and therapeutic potential.
2014,
Pubmed