1158849-73-0

Basic information

• Product Name: 8-(4-phenoxybutoxy)psoralen
• CAS NO: 1158849-73-0
• Molecular Weight: 350.371
• Mol File: 1158849-73-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 8-(4-phenoxybutoxy)psoralen(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(4-phenoxybutoxy)psoralen(1158849-73-0)
• EPA Substance Registry System: 8-(4-phenoxybutoxy)psoralen(1158849-73-0)

Safety Data

• Hazardous Substances Data: 1158849-73-0(Hazardous Substances Data)

Upstream product

• 2009-24-7 8-hydroxypsoralen 
• 1200-03-9 4-bromophenyl butyl ether 

Relevant articles and documents

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.