1-[4-(DiphenylMethyl)-1-piperazinyl]-3,3-diphenyl-1-propanone Chemical Properties

Boiling point:

618.9±55.0 °C(Predicted)

Density 

1.142±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO : 50 mg/mL (108.55 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)

form 

Powder

pka

5.99±0.10(Predicted)

color 

Light yellow to yellow

1-[4-(DiphenylMethyl)-1-piperazinyl]-3,3-diphenyl-1-propanone Usage And Synthesis

Uses

An analog of Cinnarizine (C465300), a calcium channel blocker as anti-inflammatory agent.

Synthesis

Procedure for the synthesis of 1-(Diphenylmethyl)-4-(1-oxo-3,3-diphenylpropyl)piperazine: to an anhydrous dichloromethane (40 mL) solution of 1-(Diphenylmethyl)piperazine (2.08 mmol), under nitrogen protection, was added 3,3 -diphenylpropionic acid (0.472 g, 2.08 mmol). Subsequently, EDC (0.797 g, 4.16 mmol) and a catalytic amount of DMAP were added to the reaction mixture, which was stirred overnight at room temperature under nitrogen atmosphere. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was dissolved in a solvent mixture of ethyl acetate and water (10:1, 150 mL). The organic phase was washed sequentially with water (30 mL, twice) and 10% NaOH solution (30 mL), dried with anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The crude product obtained was purified by column chromatography with the eluent being a mixture of petroleum ether and ethyl acetate (3:1), and the target product 1-(diphenylmethyl)-4-(1-oxo-3,3-diphenylpropyl)piperazine was finally obtained in 78% yield.

in vivo

IC 50

N-type calcium channel: 0.11 μM (IC₅₀); L-type calcium channel: 12.2 μM (IC₅₀)

References

[1] Patent: US2004/259866, 2004, A1
[2] Patent: US6951862, 2005, B2
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6467 - 6472
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383

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