2,2-diphenyl-5-{4-[(pyridin-3-ylmethylidene)amino]piperazin-1-yl}pentanenitrile

• ChemBase ID: 177641
• Molecular Formular: C27H29N5
• Molecular Mass: 423.55266
• Monoisotopic Mass: 423.24229595
• SMILES: N#CC(c1ccccc1)(c1ccccc1)CCCN1CCN(N=Cc2cnccc2)CC1
• Canonical SMILES: N#CC(c1ccccc1)(c1ccccc1)CCCN1CCN(CC1)N=Cc1cccnc1
• InChI: InChI=1S/C27H29N5/c28-23-27(25-10-3-1-4-11-25,26-12-5-2-6-13-26)14-8-16-31-17-19-32(20-18-31)30-22-24-9-7-15-29-21-24/h1-7,9-13,15,21-22H,8,14,16-20H2
• InChIKey: QFYKXKMYVYOUNJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-diphenyl-5-{4-[(pyridin-3-ylmethylidene)amino]piperazin-1-yl}pentanenitrile
• IUPAC Traditional name: 2,2-diphenyl-5-{4-[(pyridin-3-ylmethylidene)amino]piperazin-1-yl}pentanenitrile
• Synonyms: α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile; SC 26196; PF-o6341724; SC-26196

Database IDs

• CAS Number: 218136-59-5
• PubChem SID: 164233551
• PubChem CID: 71752132

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.9279902
• LogD (pH = 7.4): 3.6242952
• Log P: 4.0699344
• Molar Refractivity: 140.5649 cm^3
• Polarizability: 49.861156 Å^3
• Polar Surface Area: 55.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S199820

A selective Δ6 desaturase inhibitor (IC50 = 0.2 μM in vitro). Displays selectivity over Δ5 and Δ9 desaturases (IC50 values are >200 μM in vitro). It exhibits anti-inflammatory properties in a mouse edema model.

REFERENCES

• Hansen-Petrik, M. et al.: Cancer Lett., 175, 157 (2002)
• Obukowicz, M.G. et al: J. Pharmacol. Exp.T her., 287, 157 (2002)
• Zhang, L.: J. Biomol. Screen., 15, 169.