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Volumn 55, Issue 4, 2012, Pages 1593-1611

Fused piperidines as a novel class of potent and orally available transient receptor potential melastatin type 8 (TRPM8) antagonists

Author keywords

[No Author keywords available]

Indexed keywords

N(4 CHLOROPHENYL) 4 PROPYL 6,7DIHYDROTHIENO[3,2 C]PYRIDINE 5(4H) CARBOXAMIDE; N(4 FLUOROPHENYL) 1 [4 (TRIFLUOROMETHYL)PHENYL] 3,4 DIHYDROISOQUINOLINE 2(1H) CARBOXAMIDE; PIPERIDINE DERIVATIVE; PROTEIN INHIBITOR; TETRAHYDROISOQUINOLINE; TRANSIENT RECEPTOR POTENTIAL CHANNEL M8; UNCLASSIFIED DRUG;

EID: 84863116635     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2013634     Document Type: Article
Times cited : (49)

References (40)
  • 1
    • 0347504835 scopus 로고    scopus 로고
    • TRP channels as cellular sensors
    • DOI 10.1038/nature02196
    • Clapham, D. E. TRP channels as cellular sensors Nature 2003, 426, 517-524 (Pubitemid 37522633)
    • (2003) Nature , vol.426 , Issue.6966 , pp. 517-524
    • Clapham, D.E.1
  • 2
    • 79959794812 scopus 로고    scopus 로고
    • Structural biology of TRP channels
    • Li, M.; Yu, Y.; Yang, J. Structural biology of TRP channels Adv. Exp. Med. Biol. 2011, 704, 1-23
    • (2011) Adv. Exp. Med. Biol. , vol.704 , pp. 1-23
    • Li, M.1    Yu, Y.2    Yang, J.3
  • 3
    • 0037824388 scopus 로고    scopus 로고
    • TRPM8 mRNA is expressed in a subset of cold-responsive trigeminal neurons from rat
    • Nealen, M. L.; Gold, M. S.; Thut, P. D.; Caterina, M. J. TRPM8 mRNA is expressed in a subset of cold-responsive trigeminal neurons from rat J. Neurophysiol. 2003, 90, 515-520 (Pubitemid 36859197)
    • (2003) Journal of Neurophysiology , vol.90 , Issue.1 , pp. 515-520
    • Nealen, M.L.1    Gold, M.S.2    Thut, P.D.3    Caterina, M.J.4
  • 5
    • 63249103446 scopus 로고    scopus 로고
    • Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol derivatives
    • Kühn, F. J. P.; Kühn, C.; Lückhoff, A. Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol derivatives J. Biol. Chem. 2009, 284, 4102-4111
    • (2009) J. Biol. Chem. , vol.284 , pp. 4102-4111
    • Kühn, F.J.P.1    Kühn, C.2    Lückhoff, A.3
  • 6
    • 84862804874 scopus 로고    scopus 로고
    • Therapeutic potential of TRPM8 modulators
    • McKemy, D. D. Therapeutic potential of TRPM8 modulators Open Access Drug Discovery J. 2010, 2, 80-87
    • (2010) Open Access Drug Discovery J. , vol.2 , pp. 80-87
    • McKemy, D.D.1
  • 7
    • 34447542435 scopus 로고    scopus 로고
    • The menthol receptor TRPM8 is the principal detector of environmental cold
    • DOI 10.1038/nature05910, PII NATURE05910
    • Bautista, D. M.; Siemens, J.; Glazer, J. M.; Tsuruda, P. R.; Basbaum, A. I.; Stucky, C. L.; Jordt, S. E.; Julius, D. The menthol receptor TRPM8 is the principal detector of environmental cold Nature 2007, 448, 204-208 (Pubitemid 47067367)
    • (2007) Nature , vol.448 , Issue.7150 , pp. 204-208
    • Bautista, D.M.1    Siemens, J.2    Glazer, J.M.3    Tsuruda, P.R.4    Basbaum, A.I.5    Stucky, C.L.6    Jordt, S.-E.7    Julius, D.8
  • 9
    • 34247487011 scopus 로고    scopus 로고
    • TRPM8 Is Required for Cold Sensation in Mice
    • DOI 10.1016/j.neuron.2007.02.024, PII S0896627307001444
    • Dhaka, A.; Murray, A. N.; Mathur, J.; Earley, T. J.; Petrus, M. J.; Patapoutian, A. TRPM8 is required for cold sensation in mice Neuron 2007, 54, 371-378 (Pubitemid 46659806)
    • (2007) Neuron , vol.54 , Issue.3 , pp. 371-378
    • Dhaka, A.1    Murray, A.N.2    Mathur, J.3    Earley, T.J.4    Petrus, M.J.5    Patapoutian, A.6
  • 10
    • 65149103072 scopus 로고    scopus 로고
    • Involvement of increased expression of transient receptor potential melastatin 8 in oxaliplatin-induced cold allodynia in mice
    • Gauchan, P.; Andoh, T.; Kato, A.; Kuraishi, Y. Involvement of increased expression of transient receptor potential melastatin 8 in oxaliplatin-induced cold allodynia in mice Neurosci. Lett. 2009, 458, 93-95
    • (2009) Neurosci. Lett. , vol.458 , pp. 93-95
    • Gauchan, P.1    Andoh, T.2    Kato, A.3    Kuraishi, Y.4
  • 11
    • 27444444858 scopus 로고    scopus 로고
    • Advances in diabetes for the millennium: New treatments for diabetic neuropathies
    • Vinik, A. I. Advances in diabetes for the millennium: New treatments for diabetic neuropathies Med. Gen. Med. 2004, 6, 13
    • (2004) Med. Gen. Med. , vol.6 , pp. 13
    • Vinik, A.I.1
  • 12
    • 0034524018 scopus 로고    scopus 로고
    • Quantitative sensory studies in complex regional pain syndrome type 1/RSD
    • DOI 10.1097/00002508-200012000-00011
    • Tahmoush, A. J.; Schwartzman, R. J.; Hopp, J. L.; Grothusen, J. R. Quantitative sensory studies in complex regional pain syndrome type 1/RSD Clin. J. Pain 2000, 16, 340-344 (Pubitemid 32046990)
    • (2000) Clinical Journal of Pain , vol.16 , Issue.4 , pp. 340-344
    • Tahmoush, A.J.1    Schwartzman, R.J.2    Hopp, J.L.3    Grothusen, J.R.4
  • 13
    • 37249065119 scopus 로고    scopus 로고
    • TRPM8 mechanism of cold allodynia after chronic nerve injury
    • DOI 10.1523/JNEUROSCI.2203-07.2007
    • Xing, H.; Chen, M.; Ling, J.; Tan, W.; Gu, J. G. TRPM8 mechanism of cold allodynia after chronic nerve injury J. Neurosci. 2007, 27, 13680-13690 (Pubitemid 350278250)
    • (2007) Journal of Neuroscience , vol.27 , Issue.50 , pp. 13680-13690
    • Xing, H.1    Chen, M.2    Ling, J.3    Tan, W.4    Gu, J.G.5
  • 16
    • 70350212466 scopus 로고    scopus 로고
    • The contribution of TRPM8 and TRA1 channels to cold allodynia and neuropathic pain
    • 10.1371/journal.pone.0007383
    • Caspani, O.; Zurborg, S.; Labuz, D.; Heppenstall., P. A. The contribution of TRPM8 and TRA1 channels to cold allodynia and neuropathic pain PLoS ONE 2009, 4, e7383 10.1371/journal.pone.0007383
    • (2009) PLoS ONE , vol.4 , pp. 7383
    • Caspani, O.1    Zurborg, S.2    Labuz, D.3    Heppenstall, P.A.4
  • 26
    • 77950865335 scopus 로고    scopus 로고
    • (-)-Menthylamine derivatives as potent and selective antagonists of transient receptor potential melastatin type-8 (TRPM8) channels
    • Ortar, G.; De Petrocellis, L.; Morera, L.; Moriello, A. S.; Orlando, P.; Morera, E.; Nalli, M.; Di Marzo, V. (-)-Menthylamine derivatives as potent and selective antagonists of transient receptor potential melastatin type-8 (TRPM8) channels Bioorg. Med. Chem. Lett. 2010, 20, 2729-2732
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 2729-2732
    • Ortar, G.1    De Petrocellis, L.2    Morera, L.3    Moriello, A.S.4    Orlando, P.5    Morera, E.6    Nalli, M.7    Di Marzo, V.8
  • 29
    • 84986532453 scopus 로고
    • A new synthesis of 4,5,6,7-tetrahydrofuro[2,3- c ]pyridines and -furo[2,3- c ]pyrrolidines
    • Arnoldi, A.; Bregante, G.; Caldirola, P.; Merlini, L.; Tamburini, B. A new synthesis of 4,5,6,7-tetrahydrofuro[2,3- c ]pyridines and -furo[2,3- c ]pyrrolidines J. Heterocycl. Chem. 1990, 27, 1169-1171
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 1169-1171
    • Arnoldi, A.1    Bregante, G.2    Caldirola, P.3    Merlini, L.4    Tamburini, B.5
  • 30
    • 0033898081 scopus 로고    scopus 로고
    • Glucose-6-phosphatase catalytic enzyme inhibitors: Synthesis and in vitro evaluation of novel 4,5,6,7-tetrahydrothieno[3,2-c]- and -[2,3-c]pyridines
    • DOI 10.1016/S0968-0896(00)00153-X, PII S096808960000153X
    • Madsen, P.; Lundbeck, J. M.; Jakobsen, P.; Varming, A. R.; Westergaard, N. Glucose-6-phosphatase catalytic enzyme inhibitors: synthesis and in vitro evaluation of novel 4,5,6,7-tetrahydrothieno[3,2- c ]- and -[2,3- c ]pyridines Bioorg. Med. Chem. 2000, 8, 2277-2289 (Pubitemid 30642752)
    • (2000) Bioorganic and Medicinal Chemistry , vol.8 , Issue.9 , pp. 2277-2289
    • Madsen, P.1    Lundbeck, J.M.2    Jakobsen, P.3    Varming, A.R.4    Westergaard, N.5
  • 31
    • 0000597733 scopus 로고
    • Organometallic ring-opening reactions of N -acyl and N -alkoxycarbonyl lactams. Synthesis of cyclic imines
    • Giovannini, A.; Savoia, D.; Umani-Ronchi, A. Organometallic ring-opening reactions of N -acyl and N -alkoxycarbonyl lactams. Synthesis of cyclic imines J. Org. Chem. 1989, 54, 228-234
    • (1989) J. Org. Chem. , vol.54 , pp. 228-234
    • Giovannini, A.1    Savoia, D.2    Umani-Ronchi, A.3
  • 32
    • 43249097508 scopus 로고    scopus 로고
    • The determination of the absolute configurations of chiral molecules using Vibrational Circular Dichroism (VCD) spectroscopy
    • DOI 10.1002/chir.20477
    • Stephens, P. J.; Devlin, F. J.; Pan, J.-J. The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy Chirality 2008, 20, 643-663 (Pubitemid 351656169)
    • (2008) Chirality , vol.20 , Issue.5 , pp. 643-663
    • Stephens, P.J.1    Devlin, F.J.2    Pan, J.-J.3
  • 33
    • 0242322522 scopus 로고    scopus 로고
    • Absolute Configuration Determination of Chiral Molecules in the Solution State Using Vibrational Circular Dichroism
    • DOI 10.1002/chir.10287
    • Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism Chirality 2003, 15, 743-758 (Pubitemid 37356644)
    • (2003) Chirality , vol.15 , Issue.9 , pp. 743-758
    • Freedman, T.B.1    Cao, X.2    Dukor, R.3    Nafie, L.A.4
  • 34
    • 0031209438 scopus 로고    scopus 로고
    • Ab initio prediction of vibrational absorption and circular dichroism spectra of chiral natural products using density functional theory: Camphor and fenchone
    • Devlin, F. J.; Stephens, P. J.; Cheeseman, J. R.; Frisch, M. J. Ab initio prediction of vibrational absorption and circular dichroism spectra of chiral natural products using density functional theory: Camphor and fenchone J. Phys. Chem. A 1997, 101, 6322-6333 (Pubitemid 127585054)
    • (1997) Journal of Physical Chemistry A , vol.101 , Issue.35 , pp. 6322-6333
    • Devlin, F.J.1    Stephens, P.J.2    Cheeseman, J.R.3    Frisch, M.J.4
  • 35
    • 0030018579 scopus 로고    scopus 로고
    • Prediction of vibrational circular dichroism spectra using density functional theory: Camphor and fenchone
    • DOI 10.1021/ja961219+
    • Devlin, F. J.; Stephens, P. J.; Cheeseman, J. R.; Frisch, M. J. Prediction of vibrational circular dichroism spectra using density functional theory: Camphor and fenchone J. Am. Chem. Soc. 1996, 118, 6327-6328 (Pubitemid 26236883)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.26 , pp. 6327-6328
    • Devlin, F.J.1    Stephens, P.J.2    Cheeseman, J.R.3    Frisch, M.J.4
  • 36
    • 0030580848 scopus 로고    scopus 로고
    • Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory
    • PII S0009261496001546
    • Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Stephens, P. J. Ab initio calculations of atomic axial tensors and vibrational rotational strengths using density functional theory Chem. Phys. Lett. 1996, 252, 211-220 (Pubitemid 126165521)
    • (1996) Chemical Physics Letters , vol.252 , Issue.3-4 , pp. 211-220
    • Cheeseman, J.R.1    Frisch, M.J.2    Devlin, F.J.3    Stephens, P.J.4
  • 38
    • 0020675813 scopus 로고
    • AG-3-5: A chemical producing sensations of cold
    • Wei, E. T.; Seid, A. AG-3-5: A chemical producing sensations of cold J. Pharm. Pharmacol. 1983, 35, 110-112 (Pubitemid 13188129)
    • (1983) Journal of Pharmacy and Pharmacology , vol.35 , Issue.2 , pp. 110-112
    • Wei, E.T.1    Seid, D.A.2


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