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
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
Dziadulewicz, Edward K.,Bevan, Stuart J.,Brain, Christopher T.,Coote, Paul R.,Culshaw, Andrew J.,Davis, Andrew J.,Edwards, Lee J.,Fisher, Adrian J.,Fox, Alyson J.,Gentry, Clive,Groarke, Alex,Hart, Terance W.,Huber, Werner,James, Iain F.,Kesingland, Adam,La Vecchia, Luigi,Loong, Yvonne,Lyothier, Isabelle,McNair, Kara,O'Farrell, Cathal,Peacock, Marcus,Portmann, Robert,Schopfer, Ulrich,Yaqoob, Mohammed,Zadrobilek, Jiri
p. 3851 - 3856
(2008/02/10)
Naphthalene derivatives
The present invention relates to novel naphthalene derivatives of formula (I), wherein R1, R2, R3 and X are as defined in the description, and preparation thereof. The compounds of formula (I) are useful as pharmaceuticals.
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(2008/06/13)
Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones
1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.
Generation and behavior of Naphthoyloxyl radicals in photocleavage of 1-(Naphthoyloxy)-2-pyridones
A series of 1- and 2-naphthoyloxyl radicals are generated from photocleavage of 1-(naphthoyloxy)-2-pyridones in acetonitrile. Introduction of a methoxy group in the naphthalene ring stabilized the naphthoyloxyl radicals to prevent decarboxylation completely and reduced remarkably their reactivities of addition to olefins and hydrogen-atom abstraction.