Preparation and antimalarial activity of semisynthetic lycorenine derivatives

• Published in: European journal of medicinal chemistry Vol. 63; pp. 722 - 730
• Main Authors: Cedrón, Juan C., Gutiérrez, David, Flores, Ninoska, Ravelo, Ángel G., Estévez-Braun, Ana
• Format: Journal Article
• Language: English
• Published: France Elsevier Masson SAS 01-05-2013
• Subjects: Amaryllidaceae alkaloids; Amaryllidaceae Alkaloids - chemical synthesis; Amaryllidaceae Alkaloids - chemistry; Amaryllidaceae Alkaloids - pharmacology; Antimalarials - chemical synthesis; Antimalarials - chemistry; Antimalarials - pharmacology; Antiplasmodial activity; Dimerization; Hippeastrine; Humans; Inhibitory Concentration 50; Lycorenine; Models, Chemical; Molecular Structure; Parasitemia - parasitology; Parasitemia - prevention & control; Parasitic Sensitivity Tests; Plasmodium falciparum - drug effects; Structure-Activity Relationship; Amaryllidaceae alkaloids; Hippeastrine; Antiplasmodial activity; Lycorenine
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2013.03.018

A set of twenty one lycorenine derivatives has been prepared from the alkaloid hippeastrine (1). The modifications performed on hippeastrine included some functional group transformations, structural simplification and preparation of dimers. All alkaloids were tested as potential antimalarial agents, being the hippeastrine dimers the most active compounds.
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•A series of lycorenine derivatives were synthesized.•The compounds were evaluated for their in vitro antimalarial activity.•Some structure–activity relationships were outlined.•The best activities were achieved with the dimeric derivatives.