114916-49-3

Upstream product

• 32940-15-1 5-methoxy-2-tetralone 
• 214633-66-6 6-methoxy-3-(3'-hydroxypropyl)-2-tetralone ethylene ketal 
• 101691-61-6 5-methoxy-3-(2-propenyl)-2-tetralone ethylene ketal 
• 101691-60-5 3-allyl-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1028273-75-7 1-benzyl-6-methoxy-1,2,3,4,4a,5-hexahydro-benzo[g]quinoline 
• 100-44-7 benzyl chloride 
• 94403-19-7 (4aS,10aR)-6-Methoxy-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline 

Relevant academic research and scientific papers

cis- and trans-N-benzyl-octahydrobenzo[g]quinolines. Adrenergic and dopaminergic activity studies

In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and α adrenoceptors. The trans N-benzyl analogues exhibited affinity at the α2 as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the α2 adrenoceptor. Enhanced activity for the α2 receptors was also exhibited by the cis N-benzylated isomers. These observations are interpreted by theoretical calculations.

N-(iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and adrenergic and dopaminergic activity studies

A series of N-(iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines was synthesized and assayed in vitro for their dopaminergic and α-adrenergic activity. Structure-activity relationship (SAR) analysis revealed that the tested benzoquinolines exhibited activity at the D1 rather than the D2 receptor sites in contrast to the D2 receptor subfamily activity reported for their aminotetralin congeners. N-Iodopropenyl substitution was apparently a decisive factor for D1 activity independent of ring substitution pattern. Considering the structural factors influencing α-adrenergic activity, in a general trend, N-iodopropenyl analogues were α1-active, with the ring- hydroxylated congeners exhibiting the highest affinity. Affinity to the α2 receptor was even higher with no detectable trend of SAR. However, a combination of the linear arrangement of the [g]-ring system, combined with the ring hydroxyl and the N-iodopropenyl substitution in compound 5c, resulted in a significant enhancement of α2 activity in this series as demonstrated by an IC50 value of 0.5 nM. A new synthetic approach to the [g]benzoquinoline system is also described.

STEROSELECTIVE SYNTHESIS OF METHOXY SUBSTITUTED 1,2,3,4,4a,5,10,10a-OCTAHYDROBENZOQUINOLINES

The preparation of the cis- and trans-isomers of 6- and 9-methoxy-1,2,3,4,4a,5,10,10a,-octahydrobenzo-quinoline is reported.The syntheses involved reductions of cyclic iminium chlorides, which afforded the diastereomers conveniently and in good yields.