Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines.
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.
Gundersen
Lise-Lotte
LL
Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, N-0315 Oslo, Norway. l.lgundersen@kjemi.uio.no
Nissen-Meyer
Jon
J
Spilsberg
Bjørn
B
D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D015169:Colony Count, Microbial; D005663:Furans / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D008264:Macrophages / Q000187:drug effects / Q000382:microbiology; D051379:Mice; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology*; D014709:Vero Cells
C452427:9-benzyl-2-chloro-6-(2-furyl)purine; D000995:Antitubercular Agents; D005663:Furans; D011687:Purines