N4-(3-Bromophenyl)-9H-indeno[2,1-d]pyrimidine-2,4-diamine

ID: ALA2047248

Max Phase: Preclinical

Molecular Formula: C17H13BrN4

Molecular Weight: 353.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(c(Nc3cccc(Br)c3)n1)-c1ccccc1C2

Standard InChI:  InChI=1S/C17H13BrN4/c18-11-5-3-6-12(9-11)20-16-15-13-7-2-1-4-10(13)8-14(15)21-17(19)22-16/h1-7,9H,8H2,(H3,19,20,21,22)

Standard InChI Key:  QVKUVEHRSYCMGZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032    3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    4.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756    4.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7857    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040    1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133    1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2470   -5.8459    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 11 12  1  0
 12  4  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 15  1  0
 13 22  2  0
 22  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047248

   ---

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: 353.22

Molecular Weight (Monoisotopic): 352.0324

AlogP: 4.14

#Rotatable Bonds: 2

Polar Surface Area: 63.83

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.18

CX Basic pKa: 6.03

CX LogP: 4.34

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.65

References

1. Gangjee A, Zhao Y, Ihnat MA, Thorpe JE, Bailey-Downs LC, Kisliuk RL..  (2012)  Novel tricyclic indeno[2,1-d]pyrimidines with dual antiangiogenic and cytotoxic activities as potent antitumor agents.,  20  (14): [PMID:22739090] [10.1016/j.bmc.2012.05.068]

2.  (2016)  Tricyclic compounds having cytostatic and/or cytotoxic activity and methods of use thereof, 

Source

Source(2):

• Scientific Literature
• BindingDB Database