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Volumn 42, Issue 12, 1999, Pages 2087-2104

Fluorination of 3-(3-(piperidin-1-yl)propyl)indoles and 3-(3-(piperazin- 1-yl)propyl)indoles gives selective human 5-HT(1D) receptor ligands with improved pharmacokinetic profiles

Author keywords

[No Author keywords available]

Indexed keywords

3 [3 (PIPERAZIN 1 YL)PROPYL]INDOLE; 3 [3 (PIPERIDIN 1 YL)PROPYL]INDOLE; ALMOTRIPTAN; ELETRIPTAN; FLUORINE; FROVATRIPTAN; INDOLE DERIVATIVE; NARATRIPTAN; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; RIZATRIPTAN; SEROTONIN 1D AGONIST; SEROTONIN 1D RECEPTOR; SUMATRIPTAN; UNCLASSIFIED DRUG; ZOLMITRIPTAN;

EID: 0033577987     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981133m     Document Type: Article
Times cited : (157)

References (56)
  • 1
    • 0026633429 scopus 로고
    • 1 receptor agonist, sumatriptan, for the acute treatment of migraine
    • 1 Receptor Agonist, Sumatriptan, for the Acute Treatment of Migraine. Drug Dev. Res. 1992, 26, 235-240.
    • (1992) Drug Dev. Res. , vol.26 , pp. 235-240
    • Feniuk, W.1    Humphrey, P.P.A.2
  • 2
    • 0026724789 scopus 로고
    • Sumatriptan: A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headaches
    • (b) Dechant, K. L.; Clissold, S. P. Sumatriptan: A review of its Pharmacodynamic and Pharmacokinetic Properties, and Therapeutic Efficacy in the Acute Treatment of Migraine and Cluster Headaches. Drugs 1992, 43, 776-798.
    • (1992) Drugs , vol.43 , pp. 776-798
    • Dechant, K.L.1    Clissold, S.P.2
  • 3
    • 0028344125 scopus 로고
    • Sumatriptan. A reappraisal of its pharmacology and therapeutic efficacy in the acute treatment of migraine and cluster headache
    • (c) Plosker, G. L.; McTavish, D.; Sumatriptan. A Reappraisal of its Pharmacology and Therapeutic Efficacy in the Acute Treatment of Migraine and Cluster Headache. Drugs 1994, 47, 622-651.
    • (1994) Drugs , vol.47 , pp. 622-651
    • Plosker, G.L.1    McTavish, D.2
  • 4
    • 0031803892 scopus 로고    scopus 로고
    • Sumatriptan: An updated review of its use in migraine
    • (d) Perry, C. M.; Markham, A. Sumatriptan: an updated review of its use in migraine. Drugs 1998, 55, 889-922.
    • (1998) Drugs , vol.55 , pp. 889-922
    • Perry, C.M.1    Markham, A.2
  • 5
    • 0028291010 scopus 로고
    • Treatment of the migraine attack
    • Silberstein, S. D. Treatment of the migraine attack. Curr. Opin. Neurol. 1994, 7, 258-263.
    • (1994) Curr. Opin. Neurol. , vol.7 , pp. 258-263
    • Silberstein, S.D.1
  • 8
    • 0030826076 scopus 로고    scopus 로고
    • 1B/D agonists: Structure activity relationship and preclinical pharmacological distinctions
    • 1B/D agonists: structure activity relationship and preclinical pharmacological distinctions. Curr. Med. Chem. 1997, 4, 295-312.
    • (1997) Curr. Med. Chem. , vol.4 , pp. 295-312
    • Yevich, J.P.1    Yocca, F.D.2
  • 12
    • 0030661668 scopus 로고    scopus 로고
    • Migraine: Current drug discovery trend
    • Meng, C. Q. Migraine: Current Drug Discovery Trend. Curr. Med. Chem. 1997, 4, 385-404.
    • (1997) Curr. Med. Chem. , vol.4 , pp. 385-404
    • Meng, C.Q.1
  • 16
    • 0028050651 scopus 로고
    • The mode of action of Sumatriptan is vascular? A debate
    • Humphrey, P. P. A.; Goadsby, P. J. The mode of action of Sumatriptan is vascular? A Debate. Cephalagia 1994, 14, 401-410.
    • (1994) Cephalagia , vol.14 , pp. 401-410
    • Humphrey, P.P.A.1    Goadsby, P.J.2
  • 17
    • 0025103363 scopus 로고
    • The antimigraine drug, sumatriptan (GR43175), selectively blocks neurogenic plasma extravasation from blood vessels in dura mater
    • (a) Buzzi, M. G.; Bonamini, M.; Moskowitz, M. A. The antimigraine drug, Sumatriptan (GR43175), selectively blocks neurogenic plasma extravasation from blood vessels in dura mater. Br. J. Pharmacol. 1990, 99, 202-206.
    • (1990) Br. J. Pharmacol. , vol.99 , pp. 202-206
    • Buzzi, M.G.1    Bonamini, M.2    Moskowitz, M.A.3
  • 18
    • 0030902898 scopus 로고    scopus 로고
    • The novel antimigraine agent rizatriptan inhibits neurogenic dural vasodilation and extravasation
    • (b) Williamson, D. J.; Shepheard, S. L.; Hill, R. G.; Hargreaves, R. J. The novel antimigraine agent rizatriptan inhibits neurogenic dural vasodilation and extravasation. Eur. J. Pharmacol. 1997, 328, 61-64.
    • (1997) Eur. J. Pharmacol. , vol.328 , pp. 61-64
    • Williamson, D.J.1    Shepheard, S.L.2    Hill, R.G.3    Hargreaves, R.J.4
  • 19
    • 0030067627 scopus 로고    scopus 로고
    • 1D agonist drugs: Selectively targetting additional sites of action
    • 1D Agonist Drugs: Selectively Targetting Additional Sites of Action. Eur. Neurol. 1996, 36, 13-18.
    • (1996) Eur. Neurol. , vol.36 , pp. 13-18
    • Martin, G.R.1
  • 20
    • 0030914002 scopus 로고    scopus 로고
    • Rizatriptan has central antinociceptive effects against durally evoked responses
    • (b) Cumberbatch, M. J.; Hill, R. G.; Hargreaves, R. J. Rizatriptan has central antinociceptive effects against durally evoked responses. Eur. J. Pharmacol. 1997, 328, 37-40.
    • (1997) Eur. J. Pharmacol. , vol.328 , pp. 37-40
    • Cumberbatch, M.J.1    Hill, R.G.2    Hargreaves, R.J.3
  • 21
    • 0028122552 scopus 로고
    • 2 receptors in serotonin-induced contractions of human isolated coronary arteries
    • 2 Receptors in Serotonin-Induced Contractions of Human Isolated Coronary Arteries. Circulation 1994, 90 (3), 1141-1153.
    • (1994) Circulation , vol.90 , Issue.3 , pp. 1141-1153
    • Kaumann, A.J.1    Frenken, M.2
  • 22
    • 0029151705 scopus 로고
    • A comparison of the contractile effects of 5-hydoxytryptamine, sumatriptan and MK-462 on human coronary artery in vitro
    • (b) Ferro, A.; Longmore, J.; Hill, R. G.; Brown, M. J. A Comparison of the Contractile Effects of 5-Hydoxytryptamine, Sumatriptan and MK-462 on Human Coronary Artery in vitro. Br. J. Pharmacol. 1995, 40, 245-250.
    • (1995) Br. J. Pharmacol. , vol.40 , pp. 245-250
    • Ferro, A.1    Longmore, J.2    Hill, R.G.3    Brown, M.J.4
  • 23
  • 24
    • 0344104525 scopus 로고    scopus 로고
    • note
    • 1B receptors, see ref 19.
  • 25
    • 0027315058 scopus 로고
    • Sumatriptan and chest pain
    • (a) Hillis, W. S.; MacIntyre, P. D. Sumatriptan and chest pain. Lancet 1993, 341, 1564-65.
    • (1993) Lancet , vol.341 , pp. 1564-1565
    • Hillis, W.S.1    MacIntyre, P.D.2
  • 26
    • 0028816276 scopus 로고
    • Cardiovascular adverse reactions to sumatriptan. Cause for concern?
    • (b) Ottervanger, J. P.; Stricker, B. H. C. Cardiovascular Adverse Reactions to Sumatriptan. Cause for Concern? CNS Drugs 1995, 3, 90-98.
    • (1995) CNS Drugs , vol.3 , pp. 90-98
    • Ottervanger, J.P.1    Stricker, B.H.C.2
  • 27
    • 0030473835 scopus 로고    scopus 로고
    • Chest symptoms after sumatriptan: A two-year clinical practice review in 735 consecutive migraine patients
    • (c) Visser, W. H.; Jaspers, N. M. W. H.; de Vriend, R. H. M.; Ferrari, M. D. Chest Symptoms after Sumatriptan: a two-year clinical practice review in 735 consecutive migraine patients. Cephalagia 1996, 16, 554-559.
    • (1996) Cephalagia , vol.16 , pp. 554-559
    • Visser, W.H.1    Jaspers, N.M.W.H.2    De Vriend, R.H.M.3    Ferrari, M.D.4
  • 28
    • 0029813854 scopus 로고    scopus 로고
    • Differential expression of sumatriptan-sensitive 5-hydroxytryptamine receptors in human trigeminal ganglia and cerebral blood vessels
    • (a) Bouchelet, I.; Cohen, Z.; Case, B.; Seguela, P.; Hamel, E. Differential Expression of Sumatriptan-Sensitive 5-Hydroxytryptamine Receptors in Human Trigeminal Ganglia and Cerebral Blood Vessels. Mol. Pharmacol. 1996, 50, 219-223.
    • (1996) Mol. Pharmacol. , vol.50 , pp. 219-223
    • Bouchelet, I.1    Cohen, Z.2    Case, B.3    Seguela, P.4    Hamel, E.5
  • 32
    • 0344104519 scopus 로고    scopus 로고
    • note
    • (b) Experimental details for the preparation of 7 are included in the Supporting Information.
  • 35
    • 0000420715 scopus 로고
    • Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes
    • Hudlicky, M. Fluorination with Diethylaminosulfur Trifluoride and Related Aminofluorosulfuranes. Org. React. 1988, 25, 513-637.
    • (1988) Org. React. , vol.25 , pp. 513-637
    • Hudlicky, M.1
  • 37
    • 0008341036 scopus 로고
    • Epoxide formation from aldehydes and ketones - A modified method for preparing the Corey-Chaykovsky reagents
    • 6-Aza-6-tert-butyloxycarbonyl-1-oxaspiro[2.5]octane (48) was prepared from 1-ter(-butyloxycarbonyl-4-piperidone and trimethylsulfoxonium iodide: Ng, J. S. Epoxide Formation From Aldehydes And Ketones - A Modified Method For Preparing The Corey-Chaykovsky Reagents. Synth. Commun. 1990, 20, 1193-1202.
    • (1990) Synth. Commun. , vol.20 , pp. 1193-1202
    • Ng, J.S.1
  • 38
    • 0008581845 scopus 로고
    • Synthesis applications of cationic aza-cope rearrangements. Stereoselective synthesis of cis- and trans-3a-Aryl-4-oxodecahydrocyclohepta[b]pyrroles
    • Overman, L. E.; Jacobsen, E. J.; Doedens, R. J. Synthesis Applications of Cationic Aza-Cope Rearrangements. Stereoselective Synthesis of cis- and trans-3a-Aryl-4-oxodecahydrocyclohepta[b]pyrroles. J. Org. Chem. 1983, 48, 3393-3400.
    • (1983) J. Org. Chem. , vol.48 , pp. 3393-3400
    • Overman, L.E.1    Jacobsen, E.J.2    Doedens, R.J.3
  • 40
    • 0000815463 scopus 로고
    • Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo2.2.21octane salts (selectfluor reagents)
    • Lal, G. S. Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclo[2.2.21octane Salts (Selectfluor Reagents). J. Org. Chem. 1993, 58, 2791-2796.
    • (1993) J. Org. Chem. , vol.58 , pp. 2791-2796
    • Lal, G.S.1
  • 41
    • 0345398375 scopus 로고    scopus 로고
    • note
    • HH couplings to H-3 anticipated when this proton is axial.
  • 42
    • 0027310982 scopus 로고
    • A convenient and efficient workup of ozonolysis reactions using triethylamine
    • Hon, Y.-S.; Lin, S.-W.; Chen, Y.-J. A Convenient And Efficient Workup Of Ozonolysis Reactions Using Triethylamine. Synth. Commun. 1963, 23, 1543-1553.
    • (1963) Synth. Commun. , vol.23 , pp. 1543-1553
    • Hon, Y.-S.1    Lin, S.-W.2    Chen, Y.-J.3
  • 43
    • 0010648671 scopus 로고
    • Synthesis of potential transition state inhibitors of succinyl C0A: Tetrahydrodipicolinate N-Succinyl-Transferase
    • Roberts, J. L.; Borgese, J.; Chan, C.; Keith, D. D.; Wei, C.-C. Synthesis of Potential Transition State Inhibitors of Succinyl C0A: Tetrahydrodipicolinate N-Succinyl-Transferase. Heterocycles 1993, 35, 115-120.
    • (1993) Heterocycles , vol.35 , pp. 115-120
    • Roberts, J.L.1    Borgese, J.2    Chan, C.3    Keith, D.D.4    Wei, C.-C.5
  • 44
    • 33947089510 scopus 로고
    • A new method for methylation of amines
    • Borch, R. F.; Hassid, A. I. A New Method for Methylation of Amines. J. Org. Chem. 1972, 37, 1673-1675.
    • (1972) J. Org. Chem. , vol.37 , pp. 1673-1675
    • Borch, R.F.1    Hassid, A.I.2
  • 46
    • 0000782034 scopus 로고
    • 2,2-difluoro-3-hydroxyesters by reformatskii reaction
    • (a) Hallinan, E. A.; Fried, J. 2,2-difluoro-3-hydroxyesters By Reformatskii Reaction. Tetrahedron Lett. 1984, 25, 2301-2302.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2301-2302
    • Hallinan, E.A.1    Fried, J.2
  • 47
    • 0025773134 scopus 로고
    • Enantioselective synthesis of β,β-difluoromalic acid via enzymic resolution of furyl substituted derivative
    • (b) Tsukamoto, T.; Yoshiyama, T.; Kitazumi, T. Enantioselective Synthesis of β,β-difluoromalic Acid via Enzymic Resolution of Furyl Substituted Derivative. Tetrahedron Assym. 1991, 2, 759-762.
    • (1991) Tetrahedron Assym. , vol.2 , pp. 759-762
    • Tsukamoto, T.1    Yoshiyama, T.2    Kitazumi, T.3
  • 48
    • 0026537894 scopus 로고
    • A general method for the synthesis of 1,1-difluoroalkylphosphonates
    • Martin, S. F.; Dean, D. W.; Wagman, A. S. A General Method for the Synthesis of 1,1-difluoroalkylphosphonates. Tetrahedron Lett. 1992, 33, 1839-1842.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1839-1842
    • Martin, S.F.1    Dean, D.W.2    Wagman, A.S.3
  • 49
    • 0344535987 scopus 로고    scopus 로고
    • note
    • (a) For a description of this assay, see ref 20.
  • 50
    • 0027313323 scopus 로고
    • 35S)-GTPγS binding mediated by human muscarinic ml-m4 receptors: Antagonist studies
    • 35S)-GTPγS binding mediated by human muscarinic ml-m4 receptors: Antagonist studies. Br. J. Pharmacol. 1993, 709, 1120-1127.
    • (1993) Br. J. Pharmacol. , vol.709 , pp. 1120-1127
    • Lazareno, S.1    Birdsall, N.J.M.2
  • 52
    • 0344104508 scopus 로고    scopus 로고
    • note
    • The structures of N,N′-dimethylpiperazine and N-methyl-4-methyl-4-fluoropiperidine were constructed from the standard fragment library in the Sybyl package (Tripos Inc., St. Louis, Missouri). Optimization was carried out with the AM1 Hamiltonian using the eigenvector following algorithm and precise convergence criteria in MOPAC 6 (Stewart, J. J. P. QCPE #455). Partial charges were calculated for the optimized structures using the ESP method and the electrostatic potential regenerated from these charges classically to produce the contours shown in Figure 1.
  • 54
    • 0011956364 scopus 로고
    • a relative to N-methylpiperidine is then easily calculated from ΔG= -RT In K. Additionally, the bond orders and localized Orbitals were printed for each of these structures.
    • (1994) J. Org. Chem. , vol.59 , pp. 5239-5245
    • Urban, J.J.1    Von Tersch, R.L.2    Famini, G.R.3
  • 55
    • 0001267759 scopus 로고
    • Protonated 3-fluoropiperidines: An unusual fluoro directing effect and a test for quantitative theories of solvation
    • Lankin, D. C.; Chandrakumar, N. S.; Shashidhar, N. R.; Spangler, D. P.; Snyder, J. P. Protonated 3-Fluoropiperidines: An Unusual Fluoro Directing Effect and a Test for Quantitative Theories of Solvation. J. Am. Chem. Soc. 1993, 115, 3356-3357.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3356-3357
    • Lankin, D.C.1    Chandrakumar, N.S.2    Shashidhar, N.R.3    Spangler, D.P.4    Snyder, J.P.5
  • 56
    • 0344535984 scopus 로고    scopus 로고
    • note
    • The binding mode of 25 and other (2-fluoropropyl)piperazines is likely to be more similar to a recently disclosed series of reversed piperidines than the piperazines based on 3: Ladduwahetty, T. Presented at Trends In Medicinal Chemistry, Society for Medicines Research, December 3, 1998, London, U.K.


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