Synthesis of isomelamines and isocyanurates and their biological evaluation.
The reaction of cyanogen bromide (1) with primary amines (2a-p), including arylmethylamines (2l-p), gave the corresponding cyanamides (3a-p). Trimerization of 3a-p gave 1,3,5-trisubstituted 2,4,6-triiminohexahydro-1,3,5-triazines (isomelamines) (4a-p), which were treated with hydrochloric acid to give the corresponding 1,3,5-trisubstituted 2,4,6-trioxohexahydro-1,3,5-triazines (isocyanurates) (5a-c, f) and 1,3,5-trisubstituted 2-imino-4,6-dioxohexahydro-1,3,5-triazines (5b'-e'). Biological evaluation of 4a-p, 5a-c,f, and 5b'-e' was carried out, and some of these compounds showed bronchodilator and positive inotropic activities.
Niwa
R
R
Institute for Life Support Technology, Yamagata Technopolis Foundation, Japan.
Kamada
H
H
Shitara
E
E
Horiuchi
J
J
Kibushi
N
N
Kato
T
T
D000818:Animals; D001993:Bronchodilator Agents / Q000737:chemistry; D003484:Cyanamide / Q000737:chemistry* / Q000494:pharmacology; D003488:Cyanogen Bromide; D006168:Guinea Pigs; D009119:Muscle Contraction; D013268:Stimulation, Chemical; D014227:Triazines / Q000737:chemistry* / Q000494:pharmacology
D001993:Bronchodilator Agents; D014227:Triazines; D003484:Cyanamide; C011907:melamine; D003488:Cyanogen Bromide