2-Chloromethyl-1,6,7-trimethyl-1H,7H-benzo[1,2-d;4,5-d']diimidazole-4,8-dione

ID: ALA158176

PubChem CID: 10540596

Max Phase: Preclinical

Molecular Formula: C12H11ClN4O2

Molecular Weight: 278.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2c(n1C)C(=O)c1c(nc(CCl)n1C)C2=O

Standard InChI:  InChI=1S/C12H11ClN4O2/c1-5-14-7-9(16(5)2)12(19)10-8(11(7)18)15-6(4-13)17(10)3/h4H2,1-3H3

Standard InChI Key:  JDXKLJMZNPIZJM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    4.7042   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -2.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -2.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250   -3.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -1.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -2.0167    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  2  1  0
  7  1  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 10  1  0
 17  9  1  0
 18 12  1  0
 19 15  1  0
 10 11  1  0
  4  5  1  0
 12  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA158176

   2-(Chloromethyl)-1,6,7-trimethylimidazo[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: 278.70

Molecular Weight (Monoisotopic): 278.0571

AlogP: 0.98

#Rotatable Bonds: 1

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: 3.30

CX LogP: 0.52

CX LogD: 0.52

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: -0.23

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