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Structure-Activity Relationships in the 8- 7,8,indole Ring System. Part 2. Effect of 8-Amino Nitrogen Substitution on Serotonin Receptor Binding and Pharmacology.-In continuation of the preceding paper a series of nonformylated (I) and formylated analogues (II) (ca. 30 examples) of the potent and selective agonist (IIa) is prepared in which the dipropylamino group is modified. The substituent influence of these compounds (as racemic mixtures or in some cases in optically pure form) on the in vitro receptor binding with respect to the 5-HT1A, 5-HT1Dα, 5-HT1D. beta., and dopamine D2 and D3 sites as well as their in vivo pharmacology in reserpinized rats is investigated. Nearly all of these analogues exhibit excellent activity for the 5-HT1A receptor and good selectivity for serotonine over dopamine sites. Generally, the (R)-enantiomers possess the superior receptor affinity, and those analogues having a good affinity for 5-HT1A also show clear agonist pharmacology. -(ENNIS, M. D.; STJERNLOEF, P.; HOFFMAN, R. L.; GHAZAL, N. B.; SMITH, M. W.; SVENSSON, K.; WIKSTROEM, H.; HAADSMA-SVENSSON, S. R.; LIN, C.-H.; J.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Structure-Activity Relationships in the 8- 7,8,indole Ring System. Part 1. Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes.-A series of 1-and 4-substituted analogues such as (I) and (II), resp., (ca. 20 examples), and N-3-methylated derivatives of the potent 5-HTIA agonist (Ia) is prepared (in some cases in optically pure form). The analogues are investigated with respect to their in vitro binding activity to the serotonin 5-HT1A, 5-HT1Dα and 5-HT1Dβ and the dopamine D2 and D3 receptors, as well as to their in vivo agonist activity in reserpine-pretreated rats. All compounds are more or less selective for the 5-HT1A receptor. The substitution of the aldehyde group in (Ia) or (IIb) (equipotent to (Ia)) by other groups as shown in (Ib) to (If) decreases the affinity, while the introduction of the fluorine atom in the C-4 position does not change the pharmacological response. The affinity loss of N-methylated derivatives shows that the indole NH-moiety is crucial for drug-receptor interaction. -(STJERNLOEF, P.; ENNIS, M. D.; HANSSON, L. O.; HOFFMAN, R. L.; GHAZAL, N. B.; SUNDELL, S.; SMITH, M. W.; SVENSSON, K.; CARLSSON, A.; WIKSTROEM, H.; J. Med. Chem. 38 (1995) 12, 2202-2216; Dep. Pharm., Univ., S-413 90 Goeteborg, Swed.; EN) 1

Efficient New Syntheses of (+)-and (-)-Anatoxin-a (VI). Revised Configuration of Resolved 9-Methyl-9-azabicyclo(4.2.1)nonan-2-one.-It is found that (+)-anatoxin-a is obtained starting from the ketone (-)-I and not from the enantiomer (+)-I as earlier claimed. -(FERGUSON, J. R.; LUMBARD, K. W.; SCHEINMANN, F.; STACHULSKI, A. V.; STJERNLOEF, P.; SUNDELL, S.; Tetrahedron Lett. 36 (1995) 48, 8867-8870; Salford Ultrafine Chem. Res.