Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in macrophages.
9-Alkyl and 9-heteroalkyl substituted derivatives of the 2-amino-6-guanidinopurine were synthesized by alkylation of 2-amino-6-chloropurine and subsequent guanidinolysis. The activity of the thus prepared compounds on murine macrophages was examined. Compounds 4a, 4b, and 4d inhibit the LPS+IFN-gamma-induced NO production in murine macrophages while compound 4h stimulates this production.
Cesnek
Michal
M
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Praha 6, Czech Republic. cesnekm@uochb.cas.cz
Holý
Antonín
A
Masojídková
Milena
M
Zídek
Zdenek
Z
D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D018925:Chemokines / Q000378:metabolism; D005260:Female; D019791:Guanidine / Q000737:chemistry*; D007371:Interferon-gamma / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000737:chemistry* / Q000187:drug effects; D051379:Mice; D008810:Mice, Inbred C57BL; D009569:Nitric Oxide / Q000096:biosynthesis*; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D018925:Chemokines; D008070:Lipopolysaccharides; D011687:Purines; D009569:Nitric Oxide; D007371:Interferon-gamma; D019791:Guanidine