6-Aziridin-1-yl-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5,8-dione

ID: ALA137209

PubChem CID: 10799416

Max Phase: Preclinical

Molecular Formula: C12H11N3O2

Molecular Weight: 229.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(N2CC2)=CC(=O)c2c1nc1n2CCC1

Standard InChI:  InChI=1S/C12H11N3O2/c16-8-6-7(14-4-5-14)12(17)10-11(8)15-3-1-2-9(15)13-10/h6H,1-5H2

Standard InChI Key:  OVRWFVWAYRXCKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 20  0  0  0  0  0  0  0  0999 V2000
    7.3723   -3.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3723   -4.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0866   -4.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0866   -3.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8054   -3.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8099   -4.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5893   -3.4244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0784   -4.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6014   -4.7613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0928   -5.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8734   -5.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8644   -4.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0853   -2.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0858   -5.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6570   -3.2732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2412   -2.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8306   -3.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  1  2  2  0
  4 13  2  0
  1  4  1  0
  3 14  2  0
  6  9  1  0
  1 15  1  0
 16 15  1  0
 17 16  1  0
 15 17  1  0
  8  7  2  0
  7  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA137209

   6-(aziridin-1-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole-5,8-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: 229.24

Molecular Weight (Monoisotopic): 229.0851

AlogP: 0.41

#Rotatable Bonds: 1

Polar Surface Area: 54.97

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.25

CX LogP: -0.26

CX LogD: -0.26

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.65

Np Likeness Score: -0.35

References

1. Zhou R, Skibo EB..  (1996)  Chemistry of the pyrrolo[1,2-alpha]benzimidazole antitumor agents: influence of the 7-substituent on the ability to alkylate DNA and inhibit topoisomerase II.,  39  (21): [PMID:8863809] [10.1021/jm960064d]

2. Fahey K, O'Donovan L, Carr M, Carty MP, Aldabbagh F..  (2010)  The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells.,  45  (5): [PMID:20122765] [10.1016/j.ejmech.2010.01.026]

Source

Source(1):

• Scientific Literature