Original scientific paper

Conformational Analysis of the D Ring of Lysergic Acid Amides and its Bioactive Conformation

Jurkica Kidrič ; Boris Kidrič Institute of Chemistry and Lek - Pharmaceutical and Chemical Works, Ljubljana, Yugoslavia
Darko Kocjan ; Boris Kidrič Institute of Chemistry and Lek - Pharmaceutical and Chemical Works, Ljubljana, Yugoslavia
Dušan Hadži ; Boris Kidrič Institute of Chemistry and Lek - Pharmaceutical and Chemical Works, Ljubljana, Yugoslavia

Abstract

1H, 13Cnuclear magnetic resonance data on simple lysergic acid amides and ergopeptines indieate eonsiderable flexibility of the D ring. The actual conformation depends upon the existence (or absence) of intramolecular hydrogen bonding between N6 and the central amide N20-H group. The results are in agreement with molecular mechanics calculations. The proposal for the bioactive conformation is based on the comparison of key geometric parameters of the possible ergolene conformers with ones derived for the conformationally restricted dopamine congeners.

Keywords

Hrčak ID:

178030

URI

https://hrcak.srce.hr/178030

Publication date:

6.3.1986.

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