104422-04-0

Usage

Uses

Used in Pharmaceutical Industry:
1H-3-Benzazepine-7,8-diol,2,3,4,5-tetrahydro-1-phenyl-3-(2-propen-1-yl)is used as a selective dopamine D1-like receptor partial agonist for its potential application in the treatment of various neurological and psychiatric disorders. Its high selectivity for D1-like receptors (with IC50 values of 197 nM) compared to D2-like receptors (with IC50 values of 2425 nM) makes it a promising candidate for targeted therapies.
Used in Research and Development:
In the field of research, 1H-3-Benzazepine-7,8-diol,2,3,4,5-tetrahydro-1-phenyl-3-(2-propen-1-yl)can be utilized as a tool compound to study the role of dopamine D1-like receptors in various physiological and pathological processes. Its central activity following systemic administration in vivo allows researchers to investigate its effects on different brain regions and neural circuits.
Used in Drug Design and Optimization:
The unique structure and selective agonist properties of 1H-3-Benzazepine-7,8-diol,2,3,4,5-tetrahydro-1-phenyl-3-(2-propen-1-yl)make it a valuable starting point for the design and optimization of new drugs targeting dopamine D1-like receptors. By modifying its chemical structure, researchers can potentially develop more potent and selective agonists or antagonists with improved pharmacokinetic and pharmacodynamic properties.

Biological Activity

Selective dopamine D 1 -like receptor partial agonist (IC 50 values are 19.7 and 2425 nM for binding to D 1 -like and D 2 -like receptors respectively). Centrally active following systemic administration in vivo .

InChI:InChI=1/C19H21NO2.BrH/c1-2-9-20-10-8-15-11-18(21)19(22)12-16(15)17(13-20)14-6-4-3-5-7-14;/h2-7,11-12,17,21-22H,1,8-10,13H2;1H

Upstream product

• 1000004-68-1 SKF 38393 
• 106-95-6 allyl bromide 
• 20012-10-6 7,8-Dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine Hydrobromide 

Downstream Products

• 135974-58-2 3-allyl-6,9-dichloro-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Relevant academic research and scientific papers

(+/-)-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

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.

Dopamine Agonists Related to 3-Allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol. 6-Position Modifications

The N-allyl derivative (SK and F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol (SK and F 82526) retains the DA-1 agonist potency of the latter compound but unlike the parent also shows substantial DA-2 agonist activity.In a previous study of N-substituted benzazepines these combined agonist effects were shown to be uniquely associated with the N-allyl group.A continuation of this research has examined dependency of combined DA-2/DA-1 agonist activities on 6=position modification with the specific objective of developing an agonist with maximum effectiveness and potency at the DA-2 receptor subtype.DA-2 agonist activity was measured in a rabbit ear artery assay, and DA-1 agonist activity was determined in an adenylate cyclase assay.Replacing chloro with bromo retains the activity pattern and the potency of the chloro compound: replacement with a hydrogen causes a decrease of both DA-1 and DA-2 receptor activating potency.Introduction of a 6-methyl group causes loss of DA-2 agonist activity and reduction in DA-1 agonist potency.Substitution with a 6-fluoro provides the best balance of DA-2 and DA-1 agonist activities; this compound was moderately in both assays.

2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE-7,8-DIONES

Novel benzazepine derivatives having central and peripheral dopaminergic activity useful in treating Parkinson's and cardiovascular diseases. The compounds have additional use as intermediates for the synthesis of other benzazepines with similar useful properties. The 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione derivatives are particularly useful.