3-(3,5-Dimethoxy-phenyl)-N*7*-[3-(4-methyl-piperazin-1-yl)-propyl]-[1,6]naphthyridine-2,7-diamine

ID: ALA191265

PubChem CID: 5330125

Max Phase: Preclinical

Molecular Formula: C24H32N6O2

Molecular Weight: 436.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(-c2cc3cnc(NCCCN4CCN(C)CC4)cc3nc2N)c1

Standard InChI:  InChI=1S/C24H32N6O2/c1-29-7-9-30(10-8-29)6-4-5-26-23-15-22-18(16-27-23)13-21(24(25)28-22)17-11-19(31-2)14-20(12-17)32-3/h11-16H,4-10H2,1-3H3,(H2,25,28)(H,26,27)

Standard InChI Key:  NLUPPEQIXOCYEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.2542   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8875   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    0.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -3.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375   -4.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9750   -0.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3250   -0.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792    2.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    0.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    3.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8  5  2  0
  9 10  2  0
 10  8  1  0
 11 27  1  0
 12 22  1  0
 13  4  2  0
 14  4  1  0
 15  7  2  0
 16 17  1  0
 17 14  2  0
 18 13  1  0
 19  2  1  0
 20 10  1  0
 21 23  1  0
 22 24  1  0
 23 11  1  0
 24 11  1  0
 25 17  1  0
 26 18  1  0
 27 28  1  0
 28 30  1  0
 29 12  1  0
 30 20  1  0
 31 26  1  0
 32 25  1  0
 15  9  1  0
  3  6  2  0
 18 16  2  0
 21 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191265

   3-(3,5-dimethoxyphenyl)-7-N-[3-(4-methylpiperazin-1-yl)propyl]-1,6-naphthyridine-2,7-diamine

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: 436.56

Molecular Weight (Monoisotopic): 436.2587

AlogP: 2.95

#Rotatable Bonds: 8

Polar Surface Area: 88.77

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.10

CX LogP: 2.00

CX LogD: 1.23

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -0.89

References

1. 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