Collect. Czech. Chem. Commun.
1990, 55, 819-832
https://doi.org/10.1135/cccc19900819
9,10-Dihydroergopeptines modified in position 6
Miloš Beran, Antonín Černý, Miroslav Kuchař, Hana Adamírová, Jiří Holubek, Jan Taimr, Jaroslav Vachek, Maria Frühaufová, Karel Řežábek, Martin Valchář and Ivan Krejčí
Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3
Abstract
9,10-Dihydroergopeptines modified in position 6 (VII-XXIII) were prepared from 9,10-dihydroergotamine (I) and 9,10-dihydroergocristine (II) which were converted via corresponding 6-demethyl-6-cyano compounds III and IV to 6-demethyl-9,10-dihydroergotamine (V) or 6-demethyl-9,10-dihydroergocristine (VI), respectively, which were then alkylated or acylated in position 6. Methylation of 6-demethyl-6-propyl compounds VIII and IX on N1 gave 1-methyl-6-demethyl-6-propyl-9,10-dihydroergotamine (XXIV) and 1-methyl-6-demethyl-6-propyl-9,10-dihydroergocristine (XXV). In the majority of the compounds their antinidation properties, affinity to α1 adrenergic receptors and D2 receptors of dopamine were studied, and in some of them the protective effect against adrenaline and noradrenaline and dopaminergic activity in vivo were also tested.
