4-(4-phenylbutoxy)-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 155006
• Molecular Formular: C21H18O4
• Molecular Mass: 334.36522
• Monoisotopic Mass: 334.12050906
• SMILES: c1ccc(cc1)CCCCOc1c2ccc(=O)oc2cc2c1cco2
• Canonical SMILES: O=c1ccc2c(o1)cc1c(c2OCCCCc2ccccc2)cco1
• InChI: InChI=1S/C21H18O4/c22-20-10-9-16-19(25-20)14-18-17(11-13-23-18)21(16)24-12-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-11,13-14H,4-5,8,12H2
• InChIKey: JJAWGNIQEOFURP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-phenylbutoxy)-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: 4-(4-phenylbutoxy)furo[3,2-g]chromen-7-one
• Synonyms: 5-(4-Phenylbutoxy)psoralen; Psora-4; 4-(4-Phenylbutoxy)-7H-furo[3,2-g][1]benzopyran-7-one; Psora 4

Database IDs

• CAS Number: 724709-68-6
• PubChem SID: 162249144; 24278012
• PubChem CID: 6603977

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.6870832
• LogD (pH = 7.4): 4.6870832
• Log P: 4.6870832
• Molar Refractivity: 95.4225 cm^3
• Polarizability: 37.64698 Å^3
• Polar Surface Area: 48.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~16 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

• Storage Condition: protect from light; under inert gas
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H413
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H18O4

DETAILS

Sigma Aldrich - P9872

Biochem/physiol Actions
The lymphocyte potassium channel Kv1.3 is regarded as a new target for immunosuppression. Psora-4 is the most potent small-molecule Kv1.3 blocker known. It blocked Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 value of 3 nM, by preferentially binding to the C-type inactivated state of the channel. It exhibited 17- to 70-fold selectivity for Kv1.3 over closely related Kv1-family channels (Kv1.1, Kv1.2, Kv1.4, and Kv1.7) with the exception of Kv1.5 (EC50, 7.7 nM) and showed no effect on human ether-a-go-go-related channel, Kv3.1, the calcium-activated K+ channels (IKCa1, SK1-SK3, and BKCa), or the neuronal NaV1.2 channel. In a test of in vivo toxicity in rats, Psora-4 did not display any signs of acute toxicity after five daily subcutaneous injections at 33 mg/kg body weight. Psora-4 selectively suppressed the proliferation of human and rat myelin-specific effector memory T cells with EC50 values of 25 and 60 nM, respectively, without persistently suppressing peripheral blood naive and central memory T cells. Because autoantigen-specific effector memory T cells contribute to the pathogenesis of T cell-mediated autoimmune diseases such as multiple sclerosis, Psora-4 and other Kv1.3 blockers may be useful as immunomodulators for the therapy of autoimmune disord.

Toronto Research Chemicals - P839700

Psora-4 is the most potent small-molecule Kv1.3 blocker known. Psora-4 and other Kv1.3 blockers may be useful as immunomodulators for the therapy of autoimmune disorders.

REFERENCES

• Vennekamp, et al.: Mol. Pharmacol. 65 1364 (2004)
• Schmitz, et al.: Mol. Pharmacol., 68, 1254 (2004)
• Li, et al.: Am. J. Physiol. Cell Physiol., 290, 345 (2004)