Synthesis and structure-activity relationship studies of tyrosine-based antagonists at the human P2X7 receptor

Bioorg Med Chem Lett. 2008 Jan 15;18(2):571-5. doi: 10.1016/j.bmcl.2007.11.077. Epub 2007 Nov 28.

Abstract

Analogues of the P2X(7) receptor antagonist KN-62, modified at the piperazine and arylsulfonyl groups, were synthesized and assayed at the human P2X(7) receptor for inhibition of BzATP-induced effects, that is, uptake of a fluorescent dye (ethidium bromide) in stably transfected HEK293 cells and IL-1beta release in differentiated THP-1 cells. Substitution of the arylsulfonyl moiety with a nitro group increased antagonistic potency relative to methyl substitution, such that compound 21 was slightly more potent than KN-62. Substitution with D-tyrosine in 36 and sterically bulky tyrosyl 2,6-dimethyl groups [corrected] in 9 enhanced antagonistic potency.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Humans
  • Purinergic P2 Receptor Antagonists*
  • Receptors, Purinergic P2X7
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tyrosine / chemistry
  • Tyrosine / pharmacology*

Substances

  • P2RX7 protein, human
  • Purinergic P2 Receptor Antagonists
  • Receptors, Purinergic P2X7
  • Tyrosine