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We describe the synthesis of 5-aminoethyl- and 6-aminomethyl-4-oxotetrahydroindoles as butyrophenone derivatives in the indole series, as potential atypical antipsychotics. The affinities of these compounds for serotonin (5-HT 2A ) and dopamine (D 2 ) receptors were evaluated in vitro. The ratios of pK i 's for 5-HT 2A /D 2 receptors may be useful for rapid screening of new compounds and assessing potential induction of extrapyramidal symptoms ; ratio values ≥1.12 (Meltzer's ratio) are predictive of an atypical antipsychotic profile. Compounds 26e (QF 0408B) and 26f (QF 0409B) showed high affinity for both D 2 and 5-HT 2A receptors, and their Meltzer's ratios were 1.32 and 1.17 respectively, while haloperidol showed a ratio of 0.93.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Conformationally Restricted Butyrophenones with Mixed Dopaminergic (D2) and Serotoninergic (5-HT2A) Affinities. Synthesis of 5-Aminoethyl and 6-Aminomethyl-4-oxotetrahydroindoles as Potential Atypical Antipsychotics.