Chemical Properties
White powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the fruit of Citrus medica L. Var. Sarcodactylis of the Rutaceae family.
Uses
A hydroxylated psoralen that acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme with an IC50 value of 24.92 and 42.93 μM, respectively. Recent studies suggest that it may have antiproliferative and anticancer properties.
Synthesis
mL) solution in dichloromethane (CH2Cl2, 3.5 mmol) was slowly added dropwise via a glass syringe to a 1 M solution of boron tribromide (BBr3, 4 mmol) in dichloromethane. The reaction mixture was stirred at 0°C for 1-2 hours. Upon completion of the reaction, the reaction was quenched by the addition of crushed ice and the reaction mixture was extracted with dichloromethane (CH2Cl2) and washed several times with water. The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated to dryness under reduced pressure to give the target phenolic compound.
References
[1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 20, p. 2593 - 2598
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 8, p. 1604 - 1610
[3] European Journal of Medicinal Chemistry, 2013, vol. 60, p. 155 - 169
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 784 - 788
[5] Patent: WO2004/37827, 2004, A1. Location in patent: Page 26
