Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

Journal of Medicinal Chemistry

Volumn 45, Issue 19, 2002, Pages 4222-4239

  Uchikawa, Osamu ^a   Fukatsu, Kohji ^a   Tokunoh, Ryosuke ^a   Kawada, Mitsuru ^a   Matsumoto, Kiyoharu ^a   Imai, Yumi ^a   Hinuma, Shuji ^a   Kato, Koki ^a   Nishikawa, Hisao ^a   Hirai, Keisuke ^a   Miyamoto, Masaomi ^a   Ohkawa, Shigenori ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC AMP; HORMONE RECEPTOR STIMULATING AGENT; INDAN DERIVATIVE; MELATONIN; MELATONIN RECEPTOR; MELATONIN RECEPTOR STIMULATING AGENT; N [2 (1,6,7,8 TETRAHYDRO 2H INDENO[5,4 B]FURAN 8 YL)ETHYL]PROPIONAMIDE; RAMELTEON; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CAT; CHEMICAL MODIFICATION; CHIRALITY; CHO CELL; CIRCADIAN RHYTHM; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; DRUG CONFORMATION; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STABILITY; DRUG SYNTHESIS; FEMALE; INSOMNIA; MALE; NEWBORN; NONHUMAN; RAT; RECEPTOR AFFINITY; REM SLEEP; SLEEP DISORDER; SLOW WAVE SLEEP; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYRIAN HAMSTER; WAKEFULNESS;

ANIMALS; BINDING SITES; CATS; CHO CELLS; CRICETINAE; CYCLIC AMP; FEMALE; HUMANS; INDANS; MALE; MELATONIN; MESOCRICETUS; MODELS, MOLECULAR; ORGAN SPECIFICITY; PITUITARY GLAND; RADIOLIGAND ASSAY; RATS; RECEPTORS, CELL SURFACE; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, MELATONIN; SLEEP; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WAKEFULNESS;

EID: 0037068471     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0201159     Document Type: Article

References (72)

1. The pineal gland and mammalian photoperiodism
2. The melatonin message: Duration versus coincidence hypotheses
3. Pineal melatonin: Cell biology of its synthesis and of its physiological interactions
4. Melatonin comes of age?
5. Vertebrate circadian and photoperiodic systems: Role of the pineal gland and melatonin
6. Effects of melatonin on vertebrate circadian systems
7. Melatonin and circadian control in mammals
8. Melatonin: Parallels in pineal gland and retina
9. Visual pathways and the central neural control of a circadian rhythm in pineal serotonin N-acetyltransferase activity
10. Effects of damage to the suprachiasmatic area of the anterior hypothalamus on the daily melatonin and cortisol rhythms in the rhesus monkey
11. Neural control of the pineal gland
12. Melatonin excretion of man and rats: Effect of time of day, sleep, pinealectomy and food consumption
13. Urinary melatonin rhythms during sleep deprivation in depressed patients and normals
14. Melatonin excretion, body temperature and subjective arousal during 64 h of sleep deprivation
15. Sleep propensity free-runs with the temperature, melatonin and cortisol rhythms in a totally blind person
16. The association between the nocturnal sleep gate and nocturnal onset of urinary 6-sulfatoxymelatonin
17. Efficacy of melatonin as a sleep-promoting agent
18. The durations of human melatonin secretion and sleep respond to changes in daylength (photoperiod)
19. Melatonin and delayed sleep phase syndrome: Ambulatory polygraphic evaluation
20. Effect of melatonin on jet lag after long haul flights
21. Melatonin in humans: Jetlag and after
22. The effect of 6-, 9-, and 11-hour time shifts on circadian rhythms: Adaptation of sleep parameters and hormonal patterns following the intake of melatonin or placebo
23. Melatonin rhythms in night shift workers
24. Melatonin in seasonal affective disorder and phototherapy
25. Plasma melatonin - An index of brain aging in humans?
26. Alterations in nocturnal serum melatonin levels in humans with growth and aging
27. The pineal grand and melatonin in relation to aging: A summary of the theories and of the data
28. Effect of inducing nocturnal serum melatonin concentrations in daytime on sleep, mood, body temperature, and performance
29. Melatonin analogues and circadian sleep disorders
30. Sleep-inducing effects of low doses of melatonin ingested in the evening
31. Low dose melatonin improves sleep in healthy middle-aged subjects
32. Improvement of sleep quality by controlled-release melatonin in benzodiazepine-treated elderly insomniacs
33. Melatonin and the immune system
34. Melatonin in relation to the antioxidative defense and immune systems: Possible implications for cell and organ transplantation
35. Effects of the pineal hormone melatonin on the proliferation and morphological characteristics of human breast cancer cells (MCF-7) in culture
36. 11C labeled melatonin
37. 11C]-melatonin in humans
38. Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melanophores
39. 1b melatonin receptor
40. Molecular dissection of two distinct actions of melatonin on the suprachiasmatic circadian clock
41. 2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms
42. 125I] iodomelatonin binding sites in Syrian hamster peripheral organs
43. 3 as the quinone reductase 2
44. Tetrahydronaphthalenic derivatives as new agonist and antagonist ligands for melatonin receptors
45. Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors
46. Synthesis and boiological activity of conformationally restricted tricyclic analogues of the hormone melatonin
47. Conformationally restrained melatonin analogues: Synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study
48. GR196429: A nonindolic agonist at high-affinity melatonin receptors
49. Mapping the melatonin receptor. 5. Melatonin. Agonists and antagonists derived from tetrahydrocyclopent[b]indoles, tetrahydrocarbazoles and hexahydrocyclohept[b]indoles
50. Pharmacophoric search and 3D-QSAR comparative molecular field analysis studies on agonists of melatonin sheep receptors
51. Synthesis of phenalene and acenaphthene derivatives as new conformationally restricted ligands for melatonin receptors
52. Synthesis of 6,7,8,9-tetrahydropyrido[2,3-b]-indolizine and 3,4-dihydro-2H-pyrido[2′,3′:4,5]pyrrolo[2,1-b][1,3]-oxazine derivatives as new melatonin receptor ligands
53. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine
54. Perhydroindan derivatives. XII. 6-Methoxyindanone and its derivatives
55. Triphenylphosphinemethylene as an olefin-forming reagent. I
56. The utility of phosphonate carbanions in olefin synthesis
57. Potential local anaesthetics. I. Basic N-(alpha-cycloalkylbenzyl)acylamides and some related compounds
58. Effect of a marine algal constituent on the growth of lettuce and rice seedlings
59. Synthesis and structural properties of the benzopentathiepins varacin and isolissoclinotoxin A
60. A convergent route to phthalideisoquinoline alkaloids via directed metalation of tertiary benzamides
61. Synthesis of derivatives structurally related to glaziovine
62. A high-yield method for the methylenation of o-dihydroxyaromatic compounds: Synthesis of methylenedioxycoumarins
63. Optimization of parameters for semiempirical methods
64. Melatonin inhibits cyclic AMP and cyclic GMP accumulation in the rat pituitary
65. Crystal structure of rhodopsin: A G protein-coupled receptor
66. 1a melatonin receptor expressed in yeast reveals domains important for receptor function
67. Chimeric melatonin MT1 and melatonin-related receptors
68. A convergent route to phthalideisoquinoline alkaloids via directed metalation of tertiary benzamides
69. Melatonin receptors in chick brain: Characterization and localization
70. 125I]-iodomelatonin labels multiple binding sites in hamster brain