8-methoxy-1-methyl-5-(4-nitrobenzyl)-4-oxo-3,4-dihydro-5H-pyridazino[4,5-b]indole

ID: ALA2088672

PubChem CID: 70684879

Max Phase: Preclinical

Molecular Formula: C19H16N4O4

Molecular Weight: 364.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c1c(C)n[nH]c(=O)c1n2Cc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C19H16N4O4/c1-11-17-15-9-14(27-2)7-8-16(15)22(18(17)19(24)21-20-11)10-12-3-5-13(6-4-12)23(25)26/h3-9H,10H2,1-2H3,(H,21,24)

Standard InChI Key:  XJJLKQCURPTAPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -4.0542  -24.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554  -25.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3407  -25.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3425  -24.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6275  -24.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272  -25.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8369  -25.7781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8374  -24.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519  -25.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282  -25.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889  -24.2661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6796  -23.5928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5015  -23.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451  -25.6916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868  -23.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274  -26.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8426  -27.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654  -27.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806  -27.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6710  -28.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8420  -28.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307  -27.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685  -24.2831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4825  -24.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867  -29.3440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762  -30.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114  -29.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13  8  1  0
  3  6  2  0
 10 14  2  0
  6  7  1  0
 13 15  1  0
  7  9  1  0
  7 16  1  0
  8  5  1  0
 16 17  1  0
  1  2  2  0
 17 18  2  0
  5  4  2  0
 18 19  1  0
  8  9  2  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
  1 23  1  0
 10 11  1  0
 23 24  1  0
 11 12  1  0
  2  3  1  0
 25 26  2  0
 25 27  1  0
 20 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2088672

   8-methoxy-1-methyl-5-[(4-nitrophenyl)methyl]-3H-pyridazino[4,5-b]indol-4-one

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: 364.36

Molecular Weight (Monoisotopic): 364.1172

AlogP: 3.15

#Rotatable Bonds: 4

Polar Surface Area: 103.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.73

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -1.33

References

1. Bruel A, Logé C, Tauzia ML, Ravache M, Le Guevel R, Guillouzo C, Lohier JF, Oliveira Santos JS, Lozach O, Meijer L, Ruchaud S, Bénédetti H, Robert JM..  (2012)  Synthesis and biological evaluation of new 5-benzylated 4-oxo-3,4-dihydro-5H-pyridazino[4,5-b]indoles as PI3Kα inhibitors.,  57  [PMID:23063566] [10.1016/j.ejmech.2012.09.001]

Source

Source(1):

• Scientific Literature