| Identification | Back Directory | [Name]
1-[4-(DiphenylMethyl)-1-piperazinyl]-3,3-diphenyl-1-propanone | [CAS]
41332-24-5 | [Synonyms]
Z160
39-1B4
CS-2371
NP 118809
NP118809 (39-1B4
39-1B4; NP-118809
NP 118809;NP118809
1-(DiphenylMethyl)-4-(1-oxo-3,3-diphenylpropyl)piperazine
Piperazine, 1-(diphenylmethyl)-4-(1-oxo-3,3-diphenylpropyl)-
1-[4-(DiphenylMethyl)-1-piperazinyl]-3,3-diphenyl-1-propanone
1-Propanone, 1-[4-(diphenylmethyl)-1-piperazinyl]-3,3-diphenyl- | [Molecular Formula]
C32H32N2O | [MDL Number]
MFCD03387795 | [MOL File]
41332-24-5.mol | [Molecular Weight]
460.61 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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]
NP118809 (25 mg/kg, i.p.) shows significant analgesic activity in the phase IIA portions of the rat formalin model[1]. NP118809 (30 mg/kg, p.o.) results in 80.3% inhibition of mechanical allodynia and 96.3% inhibition of thermal hyperalgesia in the rat spinal nerve ligation model[2]. | [IC 50]
N-type calcium channel: 0.11 μM (IC50); L-type calcium channel: 12.2 μM (IC50) | [storage]
Store at -20°C | [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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