2,6-Bis-chloromethyl-1,7-dimethyl-1H,7H-benzo[1,2-d;4,5-d']diimidazole-4,8-dione

ID: ALA158122

PubChem CID: 10267558

Max Phase: Preclinical

Molecular Formula: C12H10Cl2N4O2

Molecular Weight: 313.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(CCl)nc2c1C(=O)c1c(nc(CCl)n1C)C2=O

Standard InChI:  InChI=1S/C12H10Cl2N4O2/c1-17-5(3-13)15-7-9(17)12(20)10-8(11(7)19)16-6(4-14)18(10)2/h3-4H2,1-2H3

Standard InChI Key:  BALDHZXOSZRRLN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    4.7750   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -1.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -3.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -0.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.3042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -2.7042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  2  0
  4  2  2  0
  5  3  1  0
  6  1  1  0
  7  2  1  0
  8  1  1  0
  9  4  1  0
 10  3  1  0
 11  7  2  0
 12  6  2  0
 13  5  2  0
 14  8  2  0
 15 11  1  0
 16 12  1  0
 17 10  1  0
 18  9  1  0
 19 16  1  0
 20 15  1  0
 10 12  1  0
  4  5  1  0
 11  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA158122

   2,6-Bis(chloromethyl)-1,7-dimethylimidazo[4,5-f]benzimidazole-4,8-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: 313.14

Molecular Weight (Monoisotopic): 312.0181

AlogP: 1.41

#Rotatable Bonds: 2

Polar Surface Area: 69.78

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.27

CX LogP: 1.06

CX LogD: 1.06

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: -0.11

References

1. Schulz WG, Skibo EB..  (2000)  Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: controlling DT-diaphorase reductive inactivation with steric bulk.,  43  (4): [PMID:10691689] [10.1021/jm990210q]

Source

Source(1):

• Scientific Literature