Synthesis and antimalarial activity of new haemanthamine-type derivatives

Juan C. Cedrón, David Gutiérrez, Esther Ninoska Flores Quisbert Flores Quisbert, Ángel G. Ravelo, Ana Estévez-Braun

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27 Scopus citations

Abstract

Thirty one derivatives were prepared from the natural alkaloids haemanthamine (1), haemanthidine (2) and 11-hydroxyvittatine (3). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and some structure-activity relationships were outlined. For haemanthamine derivatives having a methoxy group at C-3, the presence of a free hydroxyl group at C-11 is important for the activity. The double bond at C-1-C-2 plays also an important role to achieve good inhibitory activity. Compound 35 with two nicotinate groups at C-3 and at C-11 was the most active compound with a IC50 = 0.8 ± 0.06 μM.

Original languageEnglish
Pages (from-to)5464-5472
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number18
DOIs
StatePublished - 15 Sep 2012

Bibliographical note

Funding Information:
This work has been partly funded by the Spanish MICINN (SAF 2009-13296-C02-01) and ICIC (Instituto Canario de Investigación del Cáncer). J.C.C. thanks Gobierno Autónomo de Canarias for a predoctoral fellowship.

Keywords

  • Amaryllidaceae alkaloids
  • Antiplasmodial activity
  • Haemanthamine

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