Acetic acid 6-acetylamino-7-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl ester

ID: ALA17683

PubChem CID: 3553249

Max Phase: Preclinical

Molecular Formula: C15H15N3O5

Molecular Weight: 317.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC1=C(C)C(=O)c2c(nc3n2CCC3OC(C)=O)C1=O

Standard InChI:  InChI=1S/C15H15N3O5/c1-6-10(16-7(2)19)14(22)11-12(13(6)21)18-5-4-9(15(18)17-11)23-8(3)20/h9H,4-5H2,1-3H3,(H,16,19)

Standard InChI Key:  BKCMRHQLNZNMFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.4417   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -2.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -1.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -3.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -1.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -2.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125   -2.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5750   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  9  2  0
  7  1  1  0
  8  2  1  0
  9  7  1  0
 10  5  1  0
 11  6  1  0
 12  3  1  0
 13 10  1  0
 14 12  1  0
 15 11  1  0
 16  7  2  0
 17 13  1  0
 18  8  2  0
 19 15  2  0
 20 17  2  0
 21  9  1  0
 22 15  1  0
 23 17  1  0
  5  4  2  0
  6  8  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA17683

   (6-acetamido-7-methyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-yl) acetate

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: 317.30

Molecular Weight (Monoisotopic): 317.1012

AlogP: 0.68

#Rotatable Bonds: 2

Polar Surface Area: 107.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.70

CX Basic pKa: 1.96

CX LogP: -1.19

CX LogD: -1.19

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 0.52

References

1. Schulz WG, Islam I, Skibo EB..  (1995)  Pyrrolo[1,2-a]benzimidazole-based quinones and iminoquinones. The role of the 3-substituent on cytotoxicity.,  38  (1): [PMID:7837221] [10.1021/jm00001a016]

2. Skibo EB, Gordon S, Bess L, Boruah R, Heileman MJ..  (1997)  Studies of pyrrolo[1,2-alpha]benzimidazolequinone DT-diaphorase substrate activity, topoisomerase II inhibition activity, and DNA reductive alkylation.,  40  (9): [PMID:9135030] [10.1021/jm960546p]

3. Islam I, Skibo EB, Dorr RT, Alberts DS..  (1991)  Structure-activity studies of antitumor agents based on pyrrolo[1,2-a]benzimidazoles: new reductive alkylating DNA cleaving agents.,  34  (10): [PMID:1920349] [10.1021/jm00114a003]

4. 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]

5. 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