AUTOFLUORESCENT FUSED-PYRIMIDINE NUCLEOSIDES: SYNTHESIS AND EVALUATION AS PERMEANTS AND INHIBITORS OF HUMAN NUCLEOSIDE TRANSPORTERS

作者：Nowak Ireneusz^*; Damaraju Vijaya L; Cass Carol E; Young James D; Robins Morris J

来源：Collection of Czechoslovak Chemical Communications, 2011, 76(12): 1395-1412.

DOI：10.1135/cccc2011061

• Alkynylpyrimidine cyclizations
• Autofluoresent nucleoside analogues
• Nucleoside transport studies
• Ring-fused pyrimidines
• Sonogashira coupling

Nucleosides with an aromatic five-membered ring heterocycle (N, O, or S) fused at C4-C5 of pyrimidin-2-one were prepared by ring closures with 5-(alkyn-1-yl)pyrimidin-2-one intermediates, heterocyclic atom replacements, and ring closure with a 5-aminocytidine derivative. Ultraviolet absorption and emission properties of the autofluorescent products enabled studies on permeation and inhibition of the trans-cellular trafficking effected by human equilibrative nucleoside transporters (hENTs). Some of the autofluorescent nucleosides were shown to be potent and selective inhibitors of human concentrative nucleoside transporters (hCNTs) in a companion study reported elsewhere.

• 出版日期2011