4-Amino-2-(2-dimethylamino-ethyl)-dibenzo[de,h]isoquinoline-1,3-dione

ID: ALA145869

PubChem CID: 10019723

Max Phase: Preclinical

Molecular Formula: C20H19N3O2

Molecular Weight: 333.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1C(=O)c2c(N)ccc3cc4ccccc4c(c23)C1=O

Standard InChI:  InChI=1S/C20H19N3O2/c1-22(2)9-10-23-19(24)17-14-6-4-3-5-12(14)11-13-7-8-15(21)18(16(13)17)20(23)25/h3-8,11H,9-10,21H2,1-2H3

Standard InChI Key:  DVQWTHIYRCEPTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.0625   -4.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -7.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -7.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -4.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -4.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -5.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -7.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  2  0
  7  6  1  0
  8  5  1  0
  9  1  1  0
 10  4  2  0
 11  8  1  0
 12 11  1  0
 13  2  2  0
 14  3  2  0
 15  7  1  0
 16 10  1  0
 17  9  1  0
 18 17  1  0
 19 10  1  0
 20  8  2  0
 21 11  2  0
 22 18  1  0
 23 18  1  0
 24 20  1  0
 25 24  2  0
  4  6  1  0
 16 15  2  0
 12  7  2  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA145869

   12-Amino-15-[2-(dimethylamino)ethyl]-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,10,12-heptaene-14,16-dione

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: 333.39

Molecular Weight (Monoisotopic): 333.1477

AlogP: 2.73

#Rotatable Bonds: 3

Polar Surface Area: 66.64

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 2.74

CX LogD: 1.59

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -0.43

References

1. Sami SM, Dorr RT, Alberts DS, Sólyom AM, Remers WA..  (1996)  2-[2'-(Dimethylamino)ethyl]-1,2-dihydro- 3H-dibenz[de,h]isoquinoline-1,3-diones with substituents at positions 4, 8, 9, 10, and 11. Synthesis, antitumor activity, and quantitative structure-activity relationships.,  39  (25): [PMID:8960558] [10.1021/jm960623g]

2. Sami SM, Dorr RT, Sólyom AM, Alberts DS, Remers WA..  (1995)  Amino-substituted 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H- dibenz[de,h]isoquinoline-1,3-diones. Synthesis, antitumor activity, and quantitative structure--activity relationship.,  38  (6): [PMID:7699715] [10.1021/jm00006a018]

3. Sharma MC, Sharma S, Sharma P, Kumar A.  (2013)  Comparative QSAR and pharmacophore modeling of substituted 2-[2-(dimethylamino) ethyl]-1, 2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones derivatives as anti-tumor activity,  22  (12): [10.1007/s00044-013-0554-z]

Source

Source(1):

• Scientific Literature