- (+/-)-3-Allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin, a New High-Affinity D1 Dopamine Receptor Ligand: Synthesis and Structure-Activity Relationship
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The 7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines form a series of compounds having a high affinity at the D1 dopamine receptor.The 6-chloro derivative has been previously shown to have enhanced affinity, selectivity, and agonist activity.In an attempt to study the effect of substitution of a 6-bromo group in place of the 6-chloro, we hawe synthesized a series of compounds and evaluaed them for their affinity for the D1 receptor.The results show that the 6-bromo derivatives have virtually identical affinities to their 6-chloro counterparts, a findingsimilar to that found in the D1 antagonist 7-halo-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine series.From the present work, 3-allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (6-Br-APB) has been identified as a suitable candidate for further in vivo studies and resolution into its active and inactive enantiomers.
- Neumeyer, John L.,Baindur, Nandkishore,Niznik, Hyman B.,Guan, H. C.,Seeman, Philip
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p. 3366 - 3371
(2007/10/02)
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- 6-HALO-3-LOWER ALKYL-7,8-DIHYDROXY-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINES
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6-Halo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines whose structures have a lower alkyl substituted at the 3 or N-position have potent and often specific anti-Parkinsonism activity by means of their central dopaminergic effect. The lead compound of the series is 6-chloro-3-methyl-1-phenyl-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-3-benzazepin e as the base or its salts such as the hydrochloride, hydrobromide or methane sulfonate.
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