1-Benzyl-3-[7-(1-methyl-1H-pyrazol-4-yl)-1,5-naphthyridin-2-yl]urea

ID: ALA3318029

PubChem CID: 52936268

Max Phase: Preclinical

Molecular Formula: C20H18N6O

Molecular Weight: 358.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(-c2cnc3ccc(NC(=O)NCc4ccccc4)nc3c2)cn1

Standard InChI:  InChI=1S/C20H18N6O/c1-26-13-16(12-23-26)15-9-18-17(21-11-15)7-8-19(24-18)25-20(27)22-10-14-5-3-2-4-6-14/h2-9,11-13H,10H2,1H3,(H2,22,24,25,27)

Standard InChI Key:  BQCBWCAJXUXWIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    8.5669   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8578   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6860   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2719   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5182   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9810   -4.3336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5182   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8132   -2.6992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6860   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8132   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2719   -3.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950   -2.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2273   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3134   -5.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1141   -5.3161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5227   -4.6069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9745   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4471   -6.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1505   -4.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4445   -3.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -4.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7378   -5.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509   -5.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1548   -5.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 16  1  0
  3 12  1  0
  7  5  1  0
 12 15  2  0
  4 14  2  0
 15  8  1  0
 10  6  2  0
 11 10  1  0
  7  3  2  0
 13  5  2  0
  8 11  2  0
  9  3  1  0
  4  9  1  0
  1  4  1  0
  1  2  1  0
  6 13  1  0
  8  5  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 18 21  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3318029

   1-Benzyl-3-[7-(1-methylpyrazol-4-yl)-1,5-naphthyridin-2-yl]urea

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.41

Molecular Weight (Monoisotopic): 358.1542

AlogP: 3.35

#Rotatable Bonds: 4

Polar Surface Area: 84.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.77

CX Basic pKa: 2.57

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -2.17

References

1. Defaux J, Antoine M, Logé C, Le Borgne M, Schuster T, Seipelt I, Aicher B, Teifel M, Günther E, Gerlach M, Marchand P..  (2014)  Discovery of (7-aryl-1,5-naphthyridin-2-yl)ureas as dual inhibitors of ERK2 and Aurora B kinases with antiproliferative activity against cancer cells.,  24  (16): [PMID:25022204] [10.1016/j.bmcl.2014.06.078]

Source

Source(1):

• Scientific Literature