N-Cinnamoylation of Antimalarial Classics: Effects of Using Acyl Groups Other than Cinnamoyl toward Dual-Stage Antimalarials

Ana Gomes, Marta Machado, Lis Lobo, Fátima Nogueira, Miguel Prudêncio, Cátia Teixeira, Paula Gomes

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

In a follow-up study to our reports of N-cinnamoylated chloroquine and quinacrine analogues as promising dual-stage antimalarial leads with high in vitro potency against both blood-stage Plasmodium falciparum and liver-stage Plasmodium berghei, we decided to investigate the effect of replacing the cinnamoyl moiety with other acyl groups. Thus, a series of N-acylated analogues were synthesized, and their activities against blood- and liver-stage Plasmodium spp. were assessed along with their in vitro cytotoxicities. Although the new N-acylated analogues were found to be somewhat less active and more cytotoxic than their N-cinnamoylated counterparts, they equally displayed nanomolar activities in vitro against blood-stage drug-sensitive and drug-resistant P. falciparum, and significant in vitro liver-stage activity against P. berghei. Therefore, it is demonstrated that simple N-acylated surrogates of classical antimalarial drugs are promising dual-stage antimalarial leads.

Original languageEnglish
Pages (from-to)1344-1349
Number of pages6
JournalChemmedchem
Volume10
Issue number8
DOIs
Publication statusPublished - 1 Aug 2015

Keywords

  • antimalarial drugs
  • chloroquine
  • cinnamic acid
  • malaria
  • quinacrine

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