5-Chloro-2-methyl-6-phenylamino-1H-benzoimidazole-4,7-dione

ID: ALA118296

PubChem CID: 10401815

Max Phase: Preclinical

Molecular Formula: C14H10ClN3O2

Molecular Weight: 287.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2c([nH]1)C(=O)/C(=N/c1ccccc1)C(Cl)=C2O

Standard InChI:  InChI=1S/C14H10ClN3O2/c1-7-16-11-12(17-7)14(20)10(9(15)13(11)19)18-8-5-3-2-4-6-8/h2-6,19H,1H3,(H,16,17)/b18-10+

Standard InChI Key:  WEBCSNRNXPNTCE-VCHYOVAHSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    1.4250   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -1.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -0.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -0.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    0.4208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -2.0542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  5  1  0
  4  2  1  0
  5  6  2  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  7  2  0
 10  3  2  0
 11  4  2  0
 12  6  1  0
 13  5  1  0
 14 10  1  0
 15  9  1  0
 16 14  2  0
 17 14  1  0
 18 17  2  0
 19 16  1  0
 20 18  1  0
  9  8  1  0
  3  4  1  0
 20 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA118296

   5-anilino-6-chloro-2-methyl-1H-benzimidazole-4,7-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: 287.71

Molecular Weight (Monoisotopic): 287.0462

AlogP: 3.15

#Rotatable Bonds: 1

Polar Surface Area: 78.34

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.12

CX Basic pKa: 5.55

CX LogP: 1.52

CX LogD: -0.08

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.85

Np Likeness Score: -0.65

References

1. Hong SY, Chung KH, You HJ, Choi IH, Chae MJ, Han JY, Jung OJ, Kang SJ, Ryu CK..  (2004)  Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation.,  14  (13): [PMID:15177474] [10.1016/j.bmcl.2004.04.051]

2. Hong SY, Kwak KW, Ryu CK, Kang SJ, Chung KH..  (2008)  Antiproliferative effects of 6-anilino-5-chloro-1H-benzo[d]imidazole-4,7-dione in vascular smooth muscle cells.,  16  (2): [PMID:17981046] [10.1016/j.bmc.2007.10.069]

3. Ryu CK, Lee Y, Park SG, You HJ, Lee RY, Lee SY, Choi S..  (2008)  3D-QSAR studies of heterocyclic quinones with inhibitory activity on vascular smooth muscle cell proliferation using pharmacophore-based alignment.,  16  (22): [PMID:18930405] [10.1016/j.bmc.2008.09.062]

Source

Source(1):

• Scientific Literature