Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in macrophages

Michal Cesnek; Antonín Holý; Milena Masojídková; Zdenek Zídek

doi:10.1016/j.bmc.2005.02.008

Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in macrophages

Bioorg Med Chem. 2005 Apr 15;13(8):2917-26. doi: 10.1016/j.bmc.2005.02.008.

Authors

Michal Cesnek¹, Antonín Holý, Milena Masojídková, Zdenek Zídek

Affiliation

¹ 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

PMID: 15781401
DOI: 10.1016/j.bmc.2005.02.008

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Survival / drug effects
Cells, Cultured
Chemokines / metabolism
Female
Guanidine / chemistry*
Interferon-gamma / pharmacology
Lipopolysaccharides / pharmacology
Macrophages / chemistry*
Macrophages / drug effects
Mice
Mice, Inbred C57BL
Nitric Oxide / biosynthesis*
Purines / chemical synthesis*
Purines / chemistry
Purines / pharmacology*

Substances

Chemokines
Lipopolysaccharides
Purines
Nitric Oxide
Interferon-gamma
Guanidine