New 2-aminopyrimidine derivatives and their antitrypanosomal and antiplasmodial activities

Michael Hoffelner, Usama Hassan, Werner Seebacher*, Johanna Dolensky, Patrick Hochegger, Marcel Kaiser, Pascal Maeser, Robert Saf, Robert Weis

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Abstract: Novel 2-aminopyrimidine derivatives were prepared from acyclic starting materials, benzylidene acetones and ammonium thiocyanates, via 5 steps, including ring closure, aromatization, S-methylation, oxidation to methylsulfonyl compounds, and formation of guanidines with suitable amines. The prepared compounds differ from each other by the substitutions of their amino group and of their phenyl ring. The 2-aminopyrimidines were tested by use of microplate assays for their in vitro activities against a causative organism of sleeping sickness, Trypanosoma brucei rhodesiense, as well as against a causative organism of malaria, Plasmodium falciparum NF54. Their cytotoxic properties were determined with L-6 cells (rat skeletal myoblasts). Some of the compounds exhibited quite good antitrypanosomal activity, and others showed excellent antiplasmodial activity. The influence of the structural modifications on these activities is discussed. Graphic abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)1375-1385
Number of pages11
JournalMonatshefte für Chemie - Chemical Monthly
Volume151
Issue number9
DOIs
Publication statusPublished - 1 Sep 2020

Keywords

  • Antiplasmodial activity
  • Antitrypanosomal activity
  • Heterocycles
  • Drug research
  • Structure-activity relationships
  • Structure–activity relationships

ASJC Scopus subject areas

  • Chemistry(all)

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