The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (Ki < 1 nM) and with > 100-fold selectivity. Although parallel structural modification in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.

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Mono-and hepta-antennated C-6 branched glycosylthioureido-cyclomaltoheptaose derivatives have been prepared efficiently by reaction, at ambient temperature, of b-d-glycopyranosyl isothiocyanates in the glucopyranose, cellobiose, and lactose series with either 6 I -amino-6 I -deoxycyclomaltoheptaose in pyridine or heptakis(6-amino-6-deoxy)cyclomaltoheptaose in water ± acetone at pH 8. The reverse strategy, which involves the corresponding glycosylamines as nucleophiles in reaction with cyclomaltoheptaose isothiocyanates, proved less satisfactory resulting in a number of by-products which hampered the purification step. The synthetic scheme was extended to alkyl and aryl isothiocyanate, electrophiles which as functional groups are of interest for the elaboration of dendritic wedges and the modification of the interaction and inclusion properties of cyclodextrins.