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Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.
J Med Chem. 2007 Aug 09; 50(16):3851-6.JM

Abstract

Selective activation of peripheral cannabinoid CB1 receptors has the potential to become a valuable therapy for chronic pain conditions as long as central nervous system effects are attenuated. A new class of cannabinoid ligands was rationally designed from known aminoalkylindole agonists and showed good binding and functional activities at human CB1 and CB2 receptors. This has led to the discovery of a novel CB1/CB2 dual agonist, naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone (13), which displays good oral bioavailability, potent antihyperalgesic activity in animal models, and limited brain penetration.

Authors+Show Affiliations

Novartis Institutes for BioMedical Research, 5 Gower Place, London, United Kingdom.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17630726

Citation

Dziadulewicz, Edward K., et al. "Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a Potent, Orally Bioavailable Human CB1/CB2 Dual Agonist With Antihyperalgesic Properties and Restricted Central Nervous System Penetration." Journal of Medicinal Chemistry, vol. 50, no. 16, 2007, pp. 3851-6.
Dziadulewicz EK, Bevan SJ, Brain CT, et al. Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration. J Med Chem. 2007;50(16):3851-6.
Dziadulewicz, E. K., Bevan, S. J., Brain, C. T., Coote, P. R., Culshaw, A. J., Davis, A. J., Edwards, L. J., Fisher, A. J., Fox, A. J., Gentry, C., Groarke, A., Hart, T. W., Huber, W., James, I. F., Kesingland, A., La Vecchia, L., Loong, Y., Lyothier, I., McNair, K., ... Zadrobilek, J. (2007). Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration. Journal of Medicinal Chemistry, 50(16), 3851-6.
Dziadulewicz EK, et al. Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a Potent, Orally Bioavailable Human CB1/CB2 Dual Agonist With Antihyperalgesic Properties and Restricted Central Nervous System Penetration. J Med Chem. 2007 Aug 9;50(16):3851-6. PubMed PMID: 17630726.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration. AU - Dziadulewicz,Edward K, AU - Bevan,Stuart J, AU - Brain,Christopher T, AU - Coote,Paul R, AU - Culshaw,Andrew J, AU - Davis,Andrew J, AU - Edwards,Lee J, AU - Fisher,Adrian J, AU - Fox,Alyson J, AU - Gentry,Clive, AU - Groarke,Alex, AU - Hart,Terance W, AU - Huber,Werner, AU - James,Iain F, AU - Kesingland,Adam, AU - La Vecchia,Luigi, AU - Loong,Yvonne, AU - Lyothier,Isabelle, AU - McNair,Kara, AU - O'Farrell,Cathal, AU - Peacock,Marcus, AU - Portmann,Robert, AU - Schopfer,Ulrich, AU - Yaqoob,Mohammed, AU - Zadrobilek,Jiri, Y1 - 2007/07/14/ PY - 2007/7/17/pubmed PY - 2007/11/10/medline PY - 2007/7/17/entrez SP - 3851 EP - 6 JF - Journal of medicinal chemistry JO - J Med Chem VL - 50 IS - 16 N2 - Selective activation of peripheral cannabinoid CB1 receptors has the potential to become a valuable therapy for chronic pain conditions as long as central nervous system effects are attenuated. A new class of cannabinoid ligands was rationally designed from known aminoalkylindole agonists and showed good binding and functional activities at human CB1 and CB2 receptors. This has led to the discovery of a novel CB1/CB2 dual agonist, naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone (13), which displays good oral bioavailability, potent antihyperalgesic activity in animal models, and limited brain penetration. SN - 0022-2623 UR - https://www.unboundmedicine.com/medline/citation/17630726/Naphthalen_1_yl__4_pentyloxynaphthalen_1_yl_methanone:_a_potent_orally_bioavailable_human_CB1/CB2_dual_agonist_with_antihyperalgesic_properties_and_restricted_central_nervous_system_penetration_ L2 - https://doi.org/10.1021/jm070317a DB - PRIME DP - Unbound Medicine ER -