Title: Functionalized chloroenamines in aminocyclopropane synthesis - XV. Synthesis of conformationally rigid analogues of [1,4′-bipiperidine]-4′-carboxamide - a common pharmacophoric group
Abstract: 6-Piperidino-3-azabicyclo[3.1.0]hexane-6-carboxamide diastereomers 5 and 7 represent conformationally rigid analogues of the pharmacophoric group 1. Compounds 5 and 7 were synthesized with high stereoselectivity via chloroenamines 12a and 13b, respectively. Introduction of a 4-(4-fluorophenyl)-4-oxobutyl moiety in 5 and 7 led to derivatives 6 and 8 which correspond to rigid conformers of Pipamperone 2, a neuroleptic drug. An X-ray structure analysis was performed for compound 6; configuration and conformation of 5 – 8 were determined 1H NMR spectroscopically. 3′,5′-Cyclopipamperone diastereomers 6 and 8 showed different affinities to dopamine receptors D2L and D3.
Publication Year: 1994
Publication Date: 1994-03-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 12
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