7-benzyl-N5-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-1,5-diamine

ID: ALA1098186

PubChem CID: 4899895

Max Phase: Preclinical

Molecular Formula: C22H22N6

Molecular Weight: 370.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n[nH]c2nc(Nc3ccccc3)c3c(c12)CCN(Cc1ccccc1)C3

Standard InChI:  InChI=1S/C22H22N6/c23-20-19-17-11-12-28(13-15-7-3-1-4-8-15)14-18(17)21(25-22(19)27-26-20)24-16-9-5-2-6-10-16/h1-10H,11-14H2,(H4,23,24,25,26,27)

Standard InChI Key:  QTEUXOQHRNHJMW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   14.6256  -24.5675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3432  -24.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0581  -24.5694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7716  -23.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7719  -24.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5624  -24.4131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0507  -23.7406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5619  -23.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8166  -22.2838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3444  -23.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0554  -22.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0516  -22.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3384  -21.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6275  -22.1005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6296  -22.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9115  -21.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9085  -20.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6212  -20.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6185  -19.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9020  -19.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1867  -19.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1929  -20.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6227  -25.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9047  -25.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8999  -26.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6111  -27.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3288  -26.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3353  -25.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  6  7  1  0
 14 16  1  0
  7  8  2  0
 16 17  1  0
  8  4  1  0
 17 18  2  0
  4  5  1  0
 18 19  1  0
  8  9  1  0
 19 20  2  0
  2  1  1  0
 20 21  1  0
 10 11  1  0
 21 22  2  0
 22 17  1  0
 10  2  2  0
  1 23  1  0
 23 24  2  0
  2  3  1  0
  3  5  2  0
  4 11  2  0
  5  6  1  0
 23 28  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098186

   7-benzyl-N5-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-1,5-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: 370.46

Molecular Weight (Monoisotopic): 370.1906

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 82.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.99

CX LogP: 3.95

CX LogD: 3.94

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -1.08

References

1. Guo C, Guzzo PR, Hadden M, Sargent BJ, Yet L, Kan Y, Palyha O, Kelly TM, Guan X, Rosko K, Gagen K, Metzger JM, Dragovic J, Lyons K, Lin LS, Nargund RP..  (2010)  Synthesis of 7-benzyl-5-(piperidin-1-yl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-1-ylamine and its analogs as bombesin receptor subtype-3 agonists.,  20  (9): [PMID:20371178] [10.1016/j.bmcl.2010.03.065]

Source

Source(1):

• Scientific Literature