The design and synthesis of YC-1 analogues as probes for soluble guanylate cyclase

Bioorg Med Chem Lett. 2006 Feb;16(3):618-21. doi: 10.1016/j.bmcl.2005.10.093. Epub 2005 Dec 1.


Soluble guanylate cyclase (sGC) is highly activated in the presence of both YC-1 (1-benzyl-3-(5'-hydroxymethyl-2'-furyl)-indazole) and CO. In this report, the design, synthesis, and activity (i.e., sGC activation) of photolabile analogues of 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole (YC-1) are presented. Initial results with 6-azido-3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole led to the synthesis of a tritium-labeled analogue. When photoactivated, this analogue labeled the alpha-subunit of sGC.

MeSH terms

  • Drug Design
  • Enzyme Activation / drug effects
  • Enzyme Activators / chemistry
  • Enzyme Activators / pharmacology
  • Guanylate Cyclase / chemistry*
  • Guanylate Cyclase / metabolism
  • Indazoles / chemical synthesis*
  • Indazoles / pharmacology
  • Molecular Structure
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / pharmacology
  • Solubility
  • Tritium / chemistry


  • Enzyme Activators
  • Indazoles
  • Platelet Aggregation Inhibitors
  • Tritium
  • 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole
  • Guanylate Cyclase