Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines

Lise-Lotte Gundersen; Jon Nissen-Meyer; Bjørn Spilsberg

doi:10.1021/jm0110284

Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines

J Med Chem. 2002 Mar 14;45(6):1383-6. doi: 10.1021/jm0110284.

Authors

Lise-Lotte Gundersen¹, Jon Nissen-Meyer, Bjørn Spilsberg

Affiliation

¹ Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, N-0315 Oslo, Norway. l.lgundersen@kjemi.uio.no

PMID: 11882008
DOI: 10.1021/jm0110284

Abstract

6-Arylpurines carrying a variety of substituents in the 9-position were prepared by Stille coupling between appropriately substituted 6-chloropurines and aryl(tributyl)tin, and the compounds were screened for antibacterial activity against Mycobacterium tuberculosis H(37)Rv. The lowest minimum inhibitory concentration value, 0.78 microg/mL, was found for 9-benzyl-2-chloro-6-(2-furyl)purine. This compound exhibited relatively low cytotoxicity, and it was active against several singly drug-resistant strains of M. tuberculosis.

Publication types

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

MeSH terms

Animals
Antitubercular Agents / chemical synthesis*
Antitubercular Agents / pharmacology*
Chlorocebus aethiops
Colony Count, Microbial
Furans / chemical synthesis
Furans / pharmacology
Humans
Macrophages / drug effects
Macrophages / microbiology
Mice
Microbial Sensitivity Tests
Mycobacterium tuberculosis / drug effects*
Purines / chemical synthesis*
Purines / pharmacology*
Vero Cells

Substances

9-benzyl-2-chloro-6-(2-furyl)purine
Antitubercular Agents
Furans
Purines