rac-2-Acetyl-8-(N-acetylamino)-6-benzyl-3-(4-chlorophenyl)-3-methyl-7-oxo-2,3-dihydro-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazine

ID: ALA2013097

PubChem CID: 57520597

Max Phase: Preclinical

Molecular Formula: C22H21ClN6O3

Molecular Weight: 452.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NN1C(=O)C(Cc2ccccc2)=NN2C1=NN(C(C)=O)C2(C)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C22H21ClN6O3/c1-14(30)24-27-20(32)19(13-16-7-5-4-6-8-16)25-29-21(27)26-28(15(2)31)22(29,3)17-9-11-18(23)12-10-17/h4-12H,13H2,1-3H3,(H,24,30)

Standard InChI Key:  RAMGPGBKDPRXDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    0.5548   -7.6519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -8.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617   -8.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -9.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640   -8.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604   -8.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -8.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -9.1501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -7.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980   -7.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121   -6.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -5.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774   -5.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622   -6.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -7.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791   -9.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6536   -7.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751   -7.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5861   -8.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5938   -8.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3126   -9.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0195   -8.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -8.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -7.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5451  -10.1281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701  -10.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869  -10.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758  -11.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3760   -8.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -9.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7998   -7.7711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -5.0133    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  7  9  1  0
  2  9  1  0
  3  8  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
  9 10  1  0
  5 16  2  0
  9 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
  6 18  1  0
 26 27  2  0
 26 28  1  0
 25 26  1  0
  4 25  1  0
  7 29  1  0
  1  2  1  0
 29 30  1  0
  2  3  1  0
 29 31  2  0
  3  4  1  0
 13 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2013097

   N-[2-acetyl-6-benzyl-3-(4-chlorophenyl)-3-methyl-7-oxo-[1,2,4]triazolo[4,3-b][1,2,4]triazin-8-yl]acetamide

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: 452.90

Molecular Weight (Monoisotopic): 452.1364

AlogP: 2.44

#Rotatable Bonds: 4

Polar Surface Area: 97.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.77

Np Likeness Score: -0.63

References

1. El Massry AM, Asal AM, Khattab SN, Haiba NS, Awney HA, Helmy M, Langer V, Amer A..  (2012)  Synthesis and structure elucidation of novel fused 1,2,4-triazine derivatives as potent inhibitors targeting CYP1A1 activity.,  20  (8): [PMID:22414679] [10.1016/j.bmc.2012.02.041]

Source

Source(1):

• Scientific Literature