870653-45-5

Basic information

• Product Name: 5-(4-PHENOXYBUTOXY)PSORALEN
• Synonyms: 5-(4-PHENOXYBUTOXY)PSORALEN;PAP-1;7H-Furo[3,2-g][1]benzopyran-7-one, 4-(4-phenoxybutoxy)-;4-(4-Phenoxybutoxy)-7H-furo[3,2-g][1]benzopyran-7-one;2-g][1]benzopyran-7-one;4-(4-phenoxybutoxy)-;7H-Furo[3;PAP-1,5-(4-Phenoxybutoxy)psoralen
• CAS NO: 870653-45-5
• Molecular Formula: C₂₁H₁₈O₅
• Molecular Weight: 350.36
• EINECS: 200-258-5
• Product Categories: API intermediates
• Mol File: 870653-45-5.mol

Chemical Properties

• Boiling Point: 555.8 °C at 760 mmHg
• Flash Point: 289.9 °C
• Appearance: white/solid
• Density: 1.269
• Vapor Pressure: 2.17E-12mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: DMSO: 9 mg/mL
• CAS DataBase Reference: 5-(4-PHENOXYBUTOXY)PSORALEN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-PHENOXYBUTOXY)PSORALEN(870653-45-5)
• EPA Substance Registry System: 5-(4-PHENOXYBUTOXY)PSORALEN(870653-45-5)

Safety Data

• Statements: 42/43
• Safety Statements: 22-36/37-45
• WGK Germany: 3
• Hazardous Substances Data: 870653-45-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-Phenoxybutoxy)psoralen is utilized as an immunosuppressive agent for the management of autoimmune diseases. Its application is primarily due to its ability to suppress effector memory T cells, which play a crucial role in the pathogenesis of various autoimmune conditions.
Used in Autoimmune Disease Management:
In the context of autoimmune diseases, 5-(4-Phenoxybutoxy)psoralen is used as a therapeutic intervention to control the activity of effector memory T cells. By doing so, it helps in mitigating the symptoms and progression of these diseases, offering a targeted approach to treatment.

Biochem/physiol Actions

Selective inhibitor of Kv1.3, voltage-gated K+ channel. PAP-1 (EC50=2 nM) potently inhibits human T effector memory cell proliferation and delayed hypersensitivity. Effective orally or intraperitoneally. 5-(4-Phenoxybutoxy)psoralen has 23-fold selectivity for Kv1.3 over Kv1.5, and 33-125-fold selectivity over other Kv1 family channels.

InChI:InChI=1/C21H18O5/c22-20-9-8-16-19(26-20)14-18-17(10-13-24-18)21(16)25-12-5-4-11-23-15-6-2-1-3-7-15/h1-3,6-10,13-14H,4-5,11-12H2

Upstream product

• 139-02-6 sodium phenoxide 
• 484-20-8 bergapten 
• 486-60-2 bergaptol 
• 1200-03-9 4-bromophenyl butyl ether 

Downstream Products

• 1158850-20-4 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione 

Relevant articles and documents

5-phenoxyalkoxypsoralens and methods for selective inhibition of the voltage gated Kv1.3 potassium channel

Compositions of matter comprising 5-phenoxyalkoxypsoralen compounds and their method of synthesis and use. The compounds are useable to treat diseases or disorders in human or animal subjects, including autoimmune diseases. The compounds inhibit potassium

Design of PAP-1, a selective small molecule Kv1.3 blocker, for the suppression of effector memory t cells in autoimmune diseases

The lymphocyte K+ channel Kv1.3 constitutes an attractive pharmacological target for the selective suppression of terminally differentiated effector memory T (TEM) cells in T cell mediated autoimmune diseases, such as multiple sclerosis and type 1 diabetes. Unfortunately, none of the existing small molecule Kv1.3 blockers is selective, and many of them, such as correolide, 4-phenyl-4-[3-(methoxyphenyl)-3-oxo-2- azapropyl] cyclohexanone, and our own compound Psora-4 inhibit the cardiac K+ channel Kv1.5. By further exploring the structure activity relationship around Psora-4 through a combination of traditional medicinal chemistry and whole-cell patch-clamp, we identified a series of new phenoxyalkoxypsoralens that exhibit 2- to 50-fold selectivity for Kv1.3 over Kv1.5, depending on their exact substitution pattern. The most potent and "druglike" compound of this series, 5-(4-phenoxybutoxy)psoralen (PAP-1), blocks Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 of 2 nM, by preferentially binding to the C-type inactivated state of the channel. PAP-1 is 23-fold selective over Kv1.5, 33- to 125-fold selective over other Kv1-family channels, and 500- to 7500-fold selective over Kv2.1, Kv3.1, Kv3.2, Kv4.2, HERG, calcium-activated K+ channels, Na+, Ca2+, and Cl- channels. PAP-1 does not exhibit cytotoxic or phototoxic effects, is negative in the Ames test, and affects cytochrome P450-dependent enzymes only at micromolar concentrations. PAP-1 potently inhibits the proliferation of human TEM cells and suppresses delayed type hypersensitivity, a TEM cell-mediated reaction, in rats. PAP-1 and several of its derivatives therefore constitute excellent new tools to further explore Kv1.3 as a target for immunosuppression and could potentially be developed into orally available immunomodulators. Copyright