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Volumn 54, Issue 12, 2011, Pages 4207-4218

Synthesis of a novel series of tricyclic dihydrofuran derivatives: Discovery of 8,9-dihydrofuro[3,2-c ]pyrazolo[1,5-a ]pyridines as melatonin receptor (MT1/MT2) ligands

Author keywords

[No Author keywords available]

Indexed keywords

1,6 DIHYDRO 2H INDENO [5,4 B] FURAN; 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDINE DERIVATIVE; MELATONIN 1 RECEPTOR; MELATONIN 2 RECEPTOR; MOLECULAR SCAFFOLD; N [2 (2 (TRIFLUOROMETHYL) 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] ACETAMIDE; N [2 (2 CYCLOPROPYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] ACETAMIDE; N [2 (2 CYCLOPROPYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] PROPANAMIDE; N [2 (2 ETHYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] ACETAMIDE; N [2 (2 ETHYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] PROPANAMIDE; N [2 (2 METHYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] ACETAMIDE; N [2 (2 METHYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] PROPANAMIDE; N [2 (2 PHENYL 7,8 DIHYDRO 1H FURO [3,2 E] BENZIMIDAZOL 1 YL) ETHYL] ACETAMIDE; N [2 (2 PHENYL 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL) ETHYL] ACETAMIDE; N [2 (7 PHENYL 1,2 DIHYDROFURO [2,3 E] IMIDAZO [1,2 A] PYRIDIN 8 YL) ETHYL] ACETAMIDE; N[2 (2 (TRIFLUOROMETHYL) 8,9 DIHYDROFURO [3,2 C] PYRAZOLO [1,5 A] PYRIDIN 1 YL)ETHYL] PROPANAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79959455122     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200385u     Document Type: Article
Times cited : (63)

References (32)
  • 1
    • 0025758136 scopus 로고
    • Pineal Melatonin: Cell Biology of Its Synthesis and of Its Physiological Interactions
    • Reiter, R. J. Pineal Melatonin: Cell Biology of Its Synthesis and of Its Physiological Interactions Endocr. Rev. 1991, 12, 151-180
    • (1991) Endocr. Rev. , vol.12 , pp. 151-180
    • Reiter, R.J.1
  • 2
  • 3
    • 11844294749 scopus 로고    scopus 로고
    • Melatonin, sleep, and circadian rhythms
    • DOI 10.1016/j.smrv.2004.11.004, PII S108707920400111X
    • Scheer, F. A. J. L.; Czeisler, C. A. Melatonin, Sleep, and Circadian Rhythms Sleep Med. Rev. 2005, 9, 5-9 (Pubitemid 40092914)
    • (2005) Sleep Medicine Reviews , vol.9 , Issue.1 , pp. 5-9
    • Scheer, F.A.J.L.1    Czeisler, C.A.2
  • 5
    • 34249072817 scopus 로고    scopus 로고
    • Effect of exogenous melatonin on sleep and motor dysfunction in Parkinson's disease: A randomized, double blind, placebo-controlled study
    • DOI 10.1007/s00415-006-0390-x
    • Medeiros, C. A.; Carvalhedo de Bruin, P. F.; Lopes, L. A.; Magalhaes, M. C.; de Lourdes Seabra, M.; de Bruin, V. M. Effect of Exogenous Melatonin on Sleep and Motor Dysfunction in Parkinsons Disease. A Randomized, Double Blind, Placebo-Controlled Study J. Neurol. 2007, 254, 459-464 (Pubitemid 46786720)
    • (2007) Journal of Neurology , vol.254 , Issue.4 , pp. 459-464
    • Medeiros, C.A.M.1    Carvalhedo De Bruin, P.F.2    Lopes, L.A.3    Magalhaes, M.C.4    De Lourdes Seabra, M.5    Sales De Bruin, V.M.6
  • 6
    • 0036479749 scopus 로고    scopus 로고
    • Melatonin as a Chronobiotic/Anticancer Agent: Cellular, Biochemical, and Molecular Mechanisms of Action and Their Implications for Circadian-Based Cancer Therapy
    • Blask, D. E.; Sauer, L. A.; Dauchy, R. T. Melatonin as a Chronobiotic/Anticancer Agent: Cellular, Biochemical, and Molecular Mechanisms of Action and Their Implications for Circadian-Based Cancer Therapy Curr. Top. Med. Chem. 2002, 2, 113-132
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 113-132
    • Blask, D.E.1    Sauer, L.A.2    Dauchy, R.T.3
  • 7
    • 27744573253 scopus 로고    scopus 로고
    • Melatonin in the Treatment of Cancer: A Systematic Review of Randomized Controlled Trials and Meta-Analysis
    • Mills, E.; Wu, P.; Seely, D.; Guyatt, G. Melatonin in the Treatment of Cancer: A Systematic Review of Randomized Controlled Trials and Meta-Analysis J. Pineal Res. 2005, 39, 360-366
    • (2005) J. Pineal Res. , vol.39 , pp. 360-366
    • Mills, E.1    Wu, P.2    Seely, D.3    Guyatt, G.4
  • 8
    • 12344325585 scopus 로고    scopus 로고
    • Systematic review and meta-analysis of the efficacy of melatonin in experimental stroke
    • DOI 10.1111/j.1600-079X.2004.00172.x
    • Macleod, M. R.; OCollins, T.; Horky, L. L.; Howells, D. W.; Donnan, G. A. Systematic Review and Meta-Analysis of the Efficacy of Melatonin in Experimental Stroke J. Pineal Res. 2005, 38, 35-41 (Pubitemid 40139308)
    • (2005) Journal of Pineal Research , vol.38 , Issue.1 , pp. 35-41
    • Macleod, M.R.1    O'Collins, T.2    Horky, L.L.3    Howells, D.W.4    Donnan, G.A.5
  • 9
    • 11844277100 scopus 로고    scopus 로고
    • The basic physiology and pathophysiology of melatonin
    • DOI 10.1016/j.smrv.2004.08.001, PII S1087079204000735
    • Claustrat, B.; Brun, J.; Chazot, G. The Basic Physiology and Pathophysiology of Melatonin Sleep Med. Rev. 2005, 9, 11-24 (Pubitemid 40092915)
    • (2005) Sleep Medicine Reviews , vol.9 , Issue.1 , pp. 11-24
    • Claustrat, B.1    Brun, J.2    Chazot, G.3
  • 10
    • 0029972613 scopus 로고    scopus 로고
    • Melatonin receptors step into the light: Cloning and classification of subtypes
    • DOI 10.1016/0165-6147(96)10005-5
    • Reppert, S. M.; Weaver, D. R.; Godson, C. Melatonin Receptors Step into the Light: Cloning and Classification of Subtypes Trends Pharmacol. Sci. 1996, 17, 100-102 (Pubitemid 26111451)
    • (1996) Trends in Pharmacological Sciences , vol.17 , Issue.3 , pp. 100-102
    • Reppert, S.M.1    Weaver, D.R.2    Godson, C.3
  • 12
    • 0030761518 scopus 로고    scopus 로고
    • Molecular dissection of two distinct actions of melatonin on the suprachiasmatic circadian clock
    • DOI 10.1016/S0896-6273(00)80350-5
    • Liu, C.; Weaver, D. R.; Jin, X.; Shearman, L. P.; Pieschl, R. L.; Gribkoff, V. K.; Reppert, S. M. Molecular Dissection of Two Distinct Actions of Melatonin on the Suprachiasmatic Circadian Clock Neuron 1997, 19, 91-102 (Pubitemid 27332996)
    • (1997) Neuron , vol.19 , Issue.1 , pp. 91-102
    • Liu, C.1    Weaver, D.R.2    Jin, X.3    Shearman, L.P.4    Pieschl, R.L.5    Gribkoff, V.K.6    Reppert, S.M.7
  • 14
    • 27644449587 scopus 로고    scopus 로고
    • 2 melatonin receptors in mammals
    • DOI 10.1385/ENDO:27:2:101
    • 2 Melatonin Receptors in Mammals Endocrine 2005, 27, 101-110 (Pubitemid 41558442)
    • (2005) Endocrine , vol.27 , Issue.2 , pp. 101-110
    • Dubocovich, M.L.1    Markowska, M.2
  • 16
    • 21844433213 scopus 로고    scopus 로고
    • Recent advances in melatonin receptor ligands
    • DOI 10.1002/ardp.200400996
    • Zlotos, D. P. Recent Advances in Melatonin Receptor Ligands Arch. Pharm. Chem. Life Sci. 2005, 338, 229-247 (Pubitemid 40957262)
    • (2005) Archiv der Pharmazie , vol.338 , Issue.5-6 , pp. 229-247
    • Zlotos, D.P.1
  • 17
    • 35048900127 scopus 로고    scopus 로고
    • Synthesis of compounds as melatonin agonists and antagonists
    • DOI 10.2174/138955707782110132
    • Garratt, P. J.; Tsotinis, A. Synthesis of Compounds as Melatonin Agonists and Antagonists Mini-Rev. Med. Chem. 2007, 7, 1075-1088 (Pubitemid 47554777)
    • (2007) Mini-Reviews in Medicinal Chemistry , vol.7 , Issue.10 , pp. 1075-1088
    • Garratt, P.J.1    Tsotinis, A.2
  • 18
    • 77952378059 scopus 로고    scopus 로고
    • Investigational Melatonin Receptor Agonists
    • Hardeland, R. Investigational Melatonin Receptor Agonists Expert Opin. Invest. Drugs 2010, 19, 747-764
    • (2010) Expert Opin. Invest. Drugs , vol.19 , pp. 747-764
    • Hardeland, R.1
  • 21
    • 60349099515 scopus 로고    scopus 로고
    • 2 Receptor Agonist: A Novel Therapeutic Drug for Sleep Disorders
    • 2 Receptor Agonist: A Novel Therapeutic Drug for Sleep Disorders CNS Neurosci. Ther. 2009, 15, 32-51
    • (2009) CNS Neurosci. Ther. , vol.15 , pp. 32-51
    • Miyamoto, M.1
  • 23
    • 77749315417 scopus 로고    scopus 로고
    • Lipophilicity in Drug Discovery
    • Waring, M. J. Lipophilicity in Drug Discovery Expert Opin. Drug Discovery 2010, 5, 235-248
    • (2010) Expert Opin. Drug Discovery , vol.5 , pp. 235-248
    • Waring, M.J.1
  • 24
    • 0021729956 scopus 로고
    • Synthesis of antimicrobial agents. VI. Studies on the synthesis of furo[3,2-b][1,8]naphthyridine derivatives
    • Hayakawa, I.; Suzuki, N.; Suzuki, K.; Tanaka, Y. Synthesis of Antimicrobial Agents. VI. Studies on the Synthesis of Furo[3,2-b][1,8] naphthyridine Derivatives Chem. Pharm. Bull. 1984, 32, 4914-4922 (Pubitemid 15151716)
    • (1984) Chemical and Pharmaceutical Bulletin , vol.32 , Issue.12 , pp. 4914-4922
    • Hayakawa, I.1    Suzuki, N.2    Suzuki, K.3    Tanaka, Y.4
  • 27
    • 0006104837 scopus 로고    scopus 로고
    • Furopyridines. XXIV[1]. Nitration, Chlorination, Acetoxylation and Cyanation of 2,3-Dihydrofuro[2,3- b ]-, -[3,2- b ]-, -[2,3- c ]- and -[3,2- c ]pyridine N -Oxides
    • Shiotani, S.; Kurosaki, M.; Taniguchi, K.; Moriyama, M. Furopyridines. XXIV[1]. Nitration, Chlorination, Acetoxylation and Cyanation of 2,3-Dihydrofuro[2,3- b ]-, -[3,2- b ]-, -[2,3- c ]- and -[3,2- c ]pyridine N -Oxides J. Hetrocycl. Chem. 1997, 34, 941-952
    • (1997) J. Hetrocycl. Chem. , vol.34 , pp. 941-952
    • Shiotani, S.1    Kurosaki, M.2    Taniguchi, K.3    Moriyama, M.4
  • 28
    • 0042839400 scopus 로고    scopus 로고
    • Highly efficient synthesis of o-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides
    • DOI 10.1021/jo034456l
    • Legault, C.; Charette, A. B. Highly efficient synthesis of O -(2,4-Dinitrophenyl)hydroxylamine. Application to the Synthesis of Substituted N -Benzoyliminopyridinium Ylides J. Org. Chem. 2003, 68, 7119-7122 (Pubitemid 37071802)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.18 , pp. 7119-7122
    • Legault, C.1    Charette, A.B.2
  • 29
    • 0030444445 scopus 로고    scopus 로고
    • 2 inhibitor
    • DOI 10.1021/jo9614452, PII S0022326396014454
    • Pawlak, J. M.; Khau, V. V.; Hutchison, D. R.; Martinelli, M. J. A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA(2) Inhibitor J. Org. Chem. 1996, 61, 9055-9059 (Pubitemid 27025714)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.25 , pp. 9055-9059
    • Pawlak, J.M.1    Khau, V.V.2    Hutchison, D.R.3    Martinelli, M.J.4
  • 30
    • 35748934487 scopus 로고    scopus 로고
    • The influence of drug-like concepts on decision-making in medicinal chemistry
    • DOI 10.1038/nrd2445, PII NRD2445
    • Leeson, P. D.; Springthorpe, B. The Influence of Drug-like Concepts on Decision-Making in Medicinal Chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890 (Pubitemid 350042396)
    • (2007) Nature Reviews Drug Discovery , vol.6 , Issue.11 , pp. 881-890
    • Leeson, P.D.1    Springthorpe, B.2
  • 31
    • 77953680038 scopus 로고    scopus 로고
    • Defining Desirable Central Nervous System Drug Space through the Alignment of Molecular Properties, in Vitro ADME, and Safety Attributes
    • Wager, T. T.; Chandrasekaran, R. Y.; Hou, X.; Troutman, M. D.; Verhoest, P. R.; Villalobos, A.; Will, Y. Defining Desirable Central Nervous System Drug Space through the Alignment of Molecular Properties, in Vitro ADME, and Safety Attributes ACS Chem. Neurosci. 2010, 1, 420-434
    • (2010) ACS Chem. Neurosci. , vol.1 , pp. 420-434
    • Wager, T.T.1    Chandrasekaran, R.Y.2    Hou, X.3    Troutman, M.D.4    Verhoest, P.R.5    Villalobos, A.6    Will, Y.7
  • 32
    • 12244294179 scopus 로고    scopus 로고
    • The sleep-promoting action of ramelteon (TAK-375) in freely moving cats
    • Miyamoto, M.; Nishikawa, H.; Doken, Y.; Hirai, K.; Uchikawa, O.; Ohkawa, S. The Sleep-Promoting Action of Ramelteon (TAK-375) in Freely Moving Cats Sleep 2004, 27, 1319-1325 (Pubitemid 44138898)
    • (2004) Sleep , vol.27 , Issue.7 , pp. 1319-1325
    • Miyamoto, M.1    Nishikawa, H.2    Doken, Y.3    Hirai, K.4    Uchikawa, O.5    Ohkawa, S.6


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