(4-Methyl-piperazin-1-yl)-[8-(3-nitro-phenyl)-[1,7]naphthyridin-6-yl]-methanone

ID: ALA161602

PubChem CID: 10547592

Max Phase: Preclinical

Molecular Formula: C20H19N5O3

Molecular Weight: 377.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C(=O)c2cc3cccnc3c(-c3cccc([N+](=O)[O-])c3)n2)CC1

Standard InChI:  InChI=1S/C20H19N5O3/c1-23-8-10-24(11-9-23)20(26)17-13-15-5-3-7-21-18(15)19(22-17)14-4-2-6-16(12-14)25(27)28/h2-7,12-13H,8-11H2,1H3

Standard InChI Key:  ODTOBENNZQIDCO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.3042    0.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -1.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375    0.8208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792    0.2333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -0.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5417   -1.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042    1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  1  2  0
  4  1  1  0
  5  3  1  0
  6  5  1  0
  7  4  2  0
  8  4  1  0
  9 12  2  0
 10  3  1  0
 11  7  1  0
 12  8  1  0
 13 20  1  0
 14  2  1  0
 15  7  1  0
 16  2  2  0
 17  5  2  0
 18  6  1  0
 19  6  1  0
 20 19  1  0
 21 18  1  0
 22  8  2  0
 23 25  2  0
 24 13  1  0
 25 22  1  0
 26 11  1  0
 27 15  2  0
 28 27  1  0
 11 10  2  0
  9 23  1  0
 26 28  2  0
 13 21  1  0
M  CHG  2   2   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA161602

   (4-Methyl-piperazin-1-yl)-[8-(3-nitro-phenyl)-[1,7]naphthyridin-6-yl]-methanone

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: 377.40

Molecular Weight (Monoisotopic): 377.1488

AlogP: 2.59

#Rotatable Bonds: 3

Polar Surface Area: 92.47

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.67

CX LogP: 2.42

CX LogD: 2.34

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -1.61

References

1. Hersperger R, Bray-French K, Mazzoni L, Müller T..  (2000)  Palladium-catalyzed cross-coupling reactions for the synthesis of 6, 8-disubstituted 1,7-naphthyridines: a novel class of potent and selective phosphodiesterase type 4D inhibitors.,  43  (4): [PMID:10691693] [10.1021/jm991094u]

Source

Source(1):

• Scientific Literature