1-tert-Butyl-3-[3-(3,5-dimethoxy-phenyl)-7-(3-morpholin-4-yl-propylamino)-[1,6]naphthyridin-2-yl]-urea

ID: ALA339856

PubChem CID: 5329004

Max Phase: Preclinical

Molecular Formula: C28H38N6O4

Molecular Weight: 522.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(-c2cc3cnc(NCCCN4CCOCC4)cc3nc2NC(=O)NC(C)(C)C)c1

Standard InChI:  InChI=1S/C28H38N6O4/c1-28(2,3)33-27(35)32-26-23(19-13-21(36-4)16-22(14-19)37-5)15-20-18-30-25(17-24(20)31-26)29-7-6-8-34-9-11-38-12-10-34/h13-18H,6-12H2,1-5H3,(H,29,30)(H2,31,32,33,35)

Standard InChI Key:  QNIMLRHYPMIYSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.3167   -1.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0000    2.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8458   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
  3  1  2  0
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  8  4  2  0
  9  8  1  0
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 34 22  1  0
 35 22  1  0
 36 22  1  0
 37 25  1  0
 38 26  1  0
  7  9  1  0
 21 19  1  0
 12 11  2  0
 32 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA339856

   1,6-Naphthyridine deriv. 20

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: 522.65

Molecular Weight (Monoisotopic): 522.2955

AlogP: 4.37

#Rotatable Bonds: 9

Polar Surface Area: 109.87

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.59

CX Basic pKa: 7.00

CX LogP: 2.95

CX LogD: 2.80

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.36

Np Likeness Score: -1.18

References

1. Thompson AM, Connolly CJ, Hamby JM, Boushelle S, Hartl BG, Amar AM, Kraker AJ, Driscoll DL, Steinkampf RW, Patmore SJ, Vincent PW, Roberts BJ, Elliott WL, Klohs W, Leopold WR, Showalter HD, Denny WA..  (2000)  3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase.,  43  (22): [PMID:11063616] [10.1021/jm000161d]

2. Thompson AM, Delaney AM, Hamby JM, Schroeder MC, Spoon TA, Crean SM, Showalter HD, Denny WA..  (2005)  Synthesis and structure-activity relationships of soluble 7-substituted 3-(3,5-dimethoxyphenyl)-1,6-naphthyridin-2-amines and related ureas as dual inhibitors of the fibroblast growth factor receptor-1 and vascular endothelial growth factor receptor-2 tyrosine kinases.,  48  (14): [PMID:16000000] [10.1021/jm0500931]

Source

Source(1):

• Scientific Literature