89242-72-8Relevant academic research and scientific papers
New 2-aminopyrimidine derivatives and their antitrypanosomal and antiplasmodial activities
Hoffelner, Michael,Hassan, Usama,Seebacher, Werner,Dolensky, Johanna,Hochegger, Patrick,Kaiser, Marcel,M?ser, Pascal,Saf, Robert,Weis, Robert
, p. 1375 - 1385 (2020/09/17)
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.].
Reactions of Monosubstituted Guanidines with 1-Phenyl-1-butane-1,3-dione
Wendelin, Winfried,Schermanz,Karl,Schweiger, Klaus,Fuchsgruber, Alfred
, p. 1371 - 1380 (2007/10/02)
Methyl-, benzyl- and phenylguanidine (2b-d) react with 1-phenyl-1,3-butanedione to yield exclusively N2-substituted 4-methyl-6-phenyl-2-pyrimidinamines 10b-d.The formation of isomeric N1-substituted 2(1H)-pyrimidinimines 11 or 12 cannot be observed.The structural formulae of 10b and c were proved by spectroscopical methods.The structure of the phenylguanidine-phenylbutanedione-condensate was determined by comparison and establishment of the identity of its picrate with an authentical sample of 10d-picrate, which had been synthetized from pyrimidinthione 13 (via methylthiopyrimidine 16*HCl).Boiling 13 with aniline in butanol yields thiodipyrimidine 15 (and not 10d). - (Keywords: 1,3-Butanedione, 1-phenyl, reactions with monosubstituted guanidines; β-Diketones, reactions with monosubstituted guanidines; Guanidines, monosubstituted, reactions with 1-phenyl-1,3-butanedione; Pyridmidine, 4-methyl-2-methylthio-6-phenyl, hydroiodide; 2-Pyrimidine-amines, 4-methyl-6-phenyl-N2-substituted, and salts; 2,2'-Thiodipyrimidine, 4,4'-dimethyl-6,6'-diphenyl)
