4-(6-{2-[(3-methylphenyl)methylidene]hydrazin-1-yl}-2-[2-(pyridin-2-yl)ethoxy]pyrimidin-4-yl)morpholine

• ChemBase ID: 160756
• Molecular Formular: C23H26N6O2
• Molecular Mass: 418.49154
• Monoisotopic Mass: 418.2117241
• SMILES: c1(nc(cc(n1)NN=Cc1cc(ccc1)C)N1CCOCC1)OCCc1ccccn1
• Canonical SMILES: Cc1cccc(c1)C=NNc1nc(OCCc2ccccn2)nc(c1)N1CCOCC1
• InChI: InChI=1S/C23H26N6O2/c1-18-5-4-6-19(15-18)17-25-28-21-16-22(29-10-13-30-14-11-29)27-23(26-21)31-12-8-20-7-2-3-9-24-20/h2-7,9,15-17H,8,10-14H2,1H3,(H,26,27,28)
• InChIKey: HSKAZIJJKRAJAV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(6-{2-[(3-methylphenyl)methylidene]hydrazin-1-yl}-2-[2-(pyridin-2-yl)ethoxy]pyrimidin-4-yl)morpholine
• IUPAC Traditional name: apilimod
• Synonyms: 3-Methylbenzaldehyde 2-[6-(4-Morpholinyl)-2-[2-(2-pyridinyl)ethoxy]-4-pyrimidinyl]hydrazone; STA 5326; Apilimod

Database IDs

• CAS Number: 541550-19-0
• PubChem SID: 162254891
• PubChem CID: 49830988

CALCULATED PROPERTIES

• Acid pKa: 13.480042
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 4.5109687
• LogD (pH = 7.4): 4.7957983
• Log P: 4.8153825
• Molar Refractivity: 123.2574 cm^3
• Polarizability: 45.039967 Å^3
• Polar Surface Area: 84.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A726600

Apilimod is a small-molecule that selectively suppresses synthesis of IL-12 and IL-23. Apilimod reduces dendritic cell infiltration in psoriasis.

REFERENCES

• Lebwohl, M., et al.: Lancet, 361, 1197 (2003)
• Gottlieb, A., et al.: J. Immunol ., 175, 2721 (2003)
• Chan, J., et al.: J. Exp. Med., 203, 2577 (2003)
• Kryczek, I., et al.: J. Immunol., 181, 4733 (2003)
• Gottlieb, A., et al.: Br. J. Dermatol., 165, 652 (20