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Volumn 42, Issue 4, 1999, Pages 677-690

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 (PYRROLIDIN 1 YL)ETHYL]INDOLE DERIVATIVE; ANTIMIGRAINE AGENT; ELETRIPTAN; NARATRIPTAN; RIZATRIPTAN; SEROTONIN 1B RECEPTOR; SEROTONIN 1D AGONIST; SUMATRIPTAN; UNCLASSIFIED DRUG; ZOLMITRIPTAN;

EID: 0033602128     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9805687     Document Type: Article
Times cited : (40)

References (45)
  • 1
    • 0028344125 scopus 로고
    • Sumatriptan: A reappraisal of its pharmacology and therapeutic efficacy in the acute treatment of migraine and cluster headache
    • 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
    • 0030961840 scopus 로고    scopus 로고
    • 5-HT receptor classification and nomenclature: Towards a harmonisation with the human genome
    • Hoyer, D.; Martin, G. 5-HT Receptor Classification and Nomenclature: Towards a Harmonisation With the Human Genome. Neuropharmacology 1997, 36, 419-428.
    • (1997) Neuropharmacology , vol.36 , pp. 419-428
    • Hoyer, D.1    Martin, G.2
  • 5
    • 0002329973 scopus 로고    scopus 로고
    • 1D receptors: Pharmacology and therapeutic potential
    • 1D Receptors: Pharmacology and Therapeutic Potential. Serotonin 1996, 1, 19-29.
    • (1996) Serotonin , vol.1 , pp. 19-29
    • Hamel, E.1
  • 9
    • 0029151705 scopus 로고
    • Comparison of the contractile effects of 5-hydroxytryptamine, sumatriptan and MK-462 on human coronary artery in vitro
    • Rizatriptan has been shown to have a lower propensity than Sumatriptan in causing contraction of isolated human artery segments: (a) Ferro, A.; Longmore, J.; Hill, R. G.; Brown, M. J. A. Comparison of the Contractile Effects of 5-Hydroxytryptamine, Sumatriptan and MK-462 on Human Coronary Artery in vitro. Br. J. Clin. Pharmacol. 1995, 40 (3), 245-251.
    • (1995) Br. J. Clin. Pharmacol. , vol.40 , Issue.3 , pp. 245-251
    • Ferro, A.1    Longmore, J.2    Hill, R.G.3    Brown, M.J.A.4
  • 11
    • 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
  • 13
    • 0030067627 scopus 로고    scopus 로고
    • 1D agonist drugs: Selectively targeting additional sites of action
    • 1D Agonist Drugs: Selectively Targeting Additional Sites of Action. Eur. Neurol. 1996, 36, 13-18.
    • (1996) Eur. Neurol. , vol.36 , pp. 13-18
    • Martin, G.R.1
  • 14
    • 0029813854 scopus 로고    scopus 로고
    • Differential expression of sumatriptan-sensitive 5-hydroxytryptamine receptors in human trigeminal ganglia and cerebral blood vessels
    • 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
  • 17
    • 84920312872 scopus 로고    scopus 로고
    • note
    • Although small, the difference in selectivity between 3b and 4 (9-fold vs 4.3-fold) is statistically significant. Further support for the inherent selectivity of the pyrrolidine base versus tryptamine is provided by the observation that the N-methyl-N-benzyl analogue of 4 is only marginally selective (4-fold).
  • 19
    • 0025122262 scopus 로고
    • Agonists and uptake inhibitors. Synthesis, absolute stereochemistry and enantioselectivity of (R)-(-)-and (S)-(+)-homo-β-proline
    • Nielsen, L.; Brehm, L.; Krogsgaard-Larsen, P. GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry and Enantioselectivity of (R)-(-)-and (S)-(+)-Homo-β-proline. J. Med. Chem. 1990, 33, 71-77.
    • (1990) J. Med. Chem. , vol.33 , pp. 71-77
    • Nielsen, L.1    Brehm, L.2    Gaba, P.3
  • 20
    • 37049111591 scopus 로고
    • Controlling the outcome of a carbocation-initiated cylisation
    • Fleming, I.; Pearce, A. Controlling the Outcome of a Carbocation-Initiated Cylisation. J. Chem. Soc., Perkin Trans. 1 1981, 251-255.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 251-255
    • Fleming, I.1    Pearce, A.2
  • 22
    • 84920312871 scopus 로고    scopus 로고
    • note
    • Note that, in the case of 12a, this operation results in inversion of the pyrrolidine C-3 chiral center.
  • 23
    • 84920312870 scopus 로고    scopus 로고
    • note
    • Synthesis of the methylene-bridged triazol-lyltryptophol required for the preparation of 22a-d is described in ref 19.
  • 24
    • 0027056036 scopus 로고
    • Synthesis of a conformationally restricted analogue of the anti-migraine drug sumatriptan
    • (a) Macor, J. E.; Blank, D. H.; Post, R. J.; Ryan, K. Synthesis of a Conformationally Restricted Analogue of the Anti-Migraine Drug Sumatriptan. Tetrahedron Lett. 1992, 33, 8011-14.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8011-8014
    • Macor, J.E.1    Blank, D.H.2    Post, R.J.3    Ryan, K.4
  • 28
    • 0030772313 scopus 로고    scopus 로고
    • Synthesis of 3-hydroxyalkylbenzo[b]furans via the palladium-catalysed heteroannulation of silyl-protected alkynols with 2-iodophenol
    • (b) Bishop, B. C.; Cottrell, I. F.; Hands, D. Synthesis of 3-Hydroxyalkylbenzo[b]furans via the Palladium-Catalysed Heteroannulation of Silyl-Protected Alkynols with 2-Iodophenol. Synthesis 1997, 1315-1320.
    • (1997) Synthesis , pp. 1315-1320
    • Bishop, B.C.1    Cottrell, I.F.2    Hands, D.3
  • 30
    • 84920312869 scopus 로고    scopus 로고
    • note
    • 35S]GTPγS is resistant to this GTPase, it accumalates in the membrane and can be measured by virtue of its radiolabel. See, for example, ref 26.
  • 31
    • 0027313323 scopus 로고
    • 35S]GTPγs binding mediated by human muscarinic m1-m4 receptors: Antagonist studies
    • 35S]GTPγS Binding Mediated by Human Muscarinic m1-m4 Receptors: Antagonist Studies. Br. J. Pharmacol. 1993, 109, 1120-1127.
    • (1993) Br. J. Pharmacol. , vol.109 , pp. 1120-1127
    • Lazareno, S.1    Birdsall, N.J.M.2
  • 32
    • 84920312868 scopus 로고    scopus 로고
    • note
    • Inflammation of the dura in animals, induced by electrical stimulation of the trigeminal ganglion, has been proposed as a possible model of migraine. See ref 10.
  • 33
    • 84920312867 scopus 로고    scopus 로고
    • note
    • 50 130 nM; maximal efficacy 101% relative to 5-HT).
  • 35
    • 84920312866 scopus 로고    scopus 로고
    • note
    • 1D receptor agonists See ref 13.
  • 36
    • 84920312865 scopus 로고    scopus 로고
    • note
    • The structures are local low-energy conformers found using the SYBYL minimization routine with the TRIPOS force field and Gasteiger-Huckel charges on the protonated species. The overlays were formed by directly overlaying the indole rings.
  • 38
    • 84920312863 scopus 로고    scopus 로고
    • note
    • 40 based upon the bacteriorhodopsin template as a starting point. Modifications to this starting conformation were made using the SYBYL modeling software from TRIPOS to produce a sensible, energetically favorable structure which conformed to our in-house results. These modifications included helix rotations and translations as well as the introduction of the loop regions between each helix including dynamics and energy minimizations (TRIPOS force field, Gasteiger-Huckel charges with neutral amino acids) with and without agonists bound.
  • 39
    • 84920312862 scopus 로고    scopus 로고
    • note
    • 1B 910 nM.
  • 40
    • 84920312861 scopus 로고    scopus 로고
    • note
    • 1F 27 nM.
  • 41
    • 84920312860 scopus 로고    scopus 로고
    • note
    • Further evidence for the contribution of the N-4-linked triazole to poor oral absorption is provided by comparison of the hepatic portal vein concentrations of 3b (135 and 31 ng/mL at 0.5 and 2 h postdose) with those of {2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl}pyrrolidine (254 and 263 ng/mL at 0.5 and 2 h pastdose).
  • 42
    • 37049116588 scopus 로고
    • Transaminations of N,N-dimethylformamide azine
    • Bartlett, R. K.; Humphrey, I. R. Transaminations of N,N-Dimethylformamide Azine. J. Chem. Soc. C 1967, 1664-1666.
    • (1967) J. Chem. Soc. C , pp. 1664-1666
    • Bartlett, R.K.1    Humphrey, I.R.2
  • 44
    • 0000191820 scopus 로고
    • Tertiary carbinamines by addition of organocerium reagents to nitriles and ketimines
    • Ciganek, E. Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines. J. Org. Chem. 1992, 57, 4521-4527.
    • (1992) J. Org. Chem. , vol.57 , pp. 4521-4527
    • Ciganek, E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.