SYNTHESIS OF R-(+)- AND S-(-)-8-HYDROXY-2-(N,N-DIPROPYLAMINO)-[2-H-3] TETRALIN - HCL (8-OH-DPAT) A 5HT1A RECEPTOR AGONIST

被引：2

作者：

ACKLAND, MJ

DRING, LG

JONES, JR

GILON, N

机构：

[1] UNIV SURREY,GUILDFORD GU2 5XH,SURREY,ENGLAND

[2] EHICS,STRASBOURG,FRANCE

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 1991年 / 29卷 / 08期

关键词：

S-(-)-8-HYDROXY-2-(N; N-DIPROPYLAMINO)-[2-H-3]TETRALIN; R-(+)-8-HYDROXY-2-(N; 8-OH-DPAT; TRITIUM LABELING; CHIRAL MOBILE PHASE CHROMATOGRAPHY; Z-GLYCYL-L-PROLINE;

D O I：

10.1002/jlcr.2580290807

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The title compounds were synthesised in 7 steps from 1,7-dihydroxynaphthalene as follows: 1,7-dihydroxynaphthalene was methylated and subjected to a Birch reduction to yield 8-methoxy-2-tetralone. Reductive amination with sodium cyanoboro[H-3]hydride and n-propylamine gave 8-methoxy-2-(n-propylamino)-[2-H-3]tetralin which was acylated and reduced to give (+/-) 8-methoxy-2-(N,N-dipropylamino)-[2-H-3]tetralin. Treatment with conc. HCl gave (+/-)-8-hydroxy-2-(N,N-dipropylamino)-[2-H-3]tetralin. The racemate was then resolved by chiral mobile phase chromatography.

引用

页码：909 / 918

页数：10

共 13 条

[11]

HAMON M, 1984, 5TH P M EUR SOC NEUR

[12] IMPROVED PREPARATION, CHROMATOGRAPHIC-SEPARATION AND X-RAY CRYSTALLOGRAPHIC DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF THE ENANTIOMERS OF 8-HYDROXY-2-(DIPROPYLAMINO)TETRALIN (8-OH DPAT) [J].