New 2-aminopyrimidine derivatives and their antitrypanosomal and antiplasmodial activities

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...

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Bibliographic Details
Published in:Monatshefte für Chemie 2020-09, Vol.151 (9), p.1375-1385
Main Authors: Hoffelner, Michael, Hassan, Usama, Seebacher, Werner, Dolensky, Johanna, Hochegger, Patrick, Kaiser, Marcel, Mäser, Pascal, Saf, Robert, Weis, Robert
Format: Article
Language:English
Subjects:
Amines
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Derivatives
Guanidines
Inorganic Chemistry
Malaria
Methylation
Organic Chemistry
Original Paper
Oxidation
Physical Chemistry
Protozoa
Theoretical and Computational Chemistry
Thiocyanates
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Summary: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
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-020-02674-7