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

ID: ALA146101

PubChem CID: 10019725

Max Phase: Preclinical

Molecular Formula: C20H19N3O2

Molecular Weight: 333.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1C(=O)c2cccc3cc4ccc(N)cc4c(c23)C1=O

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

Standard InChI Key:  SGGNFDSEAJVHLN-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
    3.3500   -5.0167    0.0000 C   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
    3.3542   -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
    4.7792   -5.8375    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
    4.0667   -7.0750    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
    4.0625   -3.7792    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
    2.6292   -4.6042    0.0000 O   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
    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
    1.2167   -6.2417    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
    5.5000   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -5.8250    0.0000 N   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
    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
    4.0542   -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
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  3  1  0
  7  4  1  0
  8  5  1  0
  9  7  1  0
 10  1  1  0
 11  8  2  0
 12  2  2  0
 13  3  2  0
 14  7  2  0
 15  9  2  0
 16 14  1  0
 17 10  1  0
 18 17  1  0
 19  6  2  0
 20 16  1  0
 21 16  2  0
 22 23  2  0
 23 19  1  0
 24 18  1  0
 25 18  1  0
  5  4  2  0
  8 22  1  0
 11  9  1  0
 15 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA146101

   4-Amino-15-[2-(dimethylamino)ethyl]-15-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,8,10,12-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: 2.09

CX LogD: 0.94

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -0.47

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