- 2-Amido-8-methoxytetralins: A Series of Nonindolic Melatonin-like Agents
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A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to complete for 2-iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of dopamine from rabbit retina.The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (Ki = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor.The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows.First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor.We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.
- Copinga, Swier,Tepper, Pieter G.,Grol, Cor J.,Horn, Alan S.,Dubocovich, Margarita L.
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p. 2891 - 2898
(2007/10/02)
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- SUBSTITUTED 2-AMIDOTETRALINS AS MELATONIN AGONISTS AND ANTAGONISTS
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The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as t
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- SUBSTITUTED 2-AMIDOTETRALINS AS MELATONIN AGONISTS AND ANTAGONISTS
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The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as t
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- SYNTHESIS AND SPECTROSCOPIC STUDY OF SOME NEW N-NAPHTHYL SUBSTITUTED 2-PHENYLACETAMIDES
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In a continuation of our previous works the conformations of new N-(1,2,3,4-tetrahydro-1-naphthyl and 1,2,3,4-tetrahydro-2-naphthyl)substituted 2-phenylacetamides, PhCH2CONHR, were investigated by vibrational, 1H n.m.r. and mass spectra.N-monosubstituted 2-phenylacetamides were obtained by using the known Schotten-Baumann reaction of acylation of synthetized amides with phenylacetic chloride.On the basis of IR-data for diluted solutions (concentration below 10-3 mol*dm-3) of N-monosubstituted 2-phenylacetamides in carbontetrachloride the exact position of N-H stretching band were established.The informations concerning the fragmentation routes, the effect of overall and partial structures as well as the influence of the amide group substituents on the fragmentation pattern, were obtained by the study of the metastable ions.The investigation of the mass spectra of the deuterium labelled and the comparison with the corresponding unlabelled compound, gave the fragmentation pattern of the various conformers.From IR, NMR and mass data it can be concluded that our synthetized N-naphthyl substituted 2-phenylacetamides exist in cis and trans form.
- Antonovic, D. G.,Nikolic, A. D.,Petrovic, S. D.
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