7,8-Dichloro-2-hydroxyphenazine5,10-dioxide

ID: ALA1288605

Chembl Id: CHEMBL1288605

PubChem CID: 136032536

Max Phase: Preclinical

Molecular Formula: C12H6Cl2N2O3

Molecular Weight: 297.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [O-][n+]1c2ccc(O)cc2[n+]([O-])c2cc(Cl)c(Cl)cc21

Standard InChI:  InChI=1S/C12H6Cl2N2O3/c13-7-4-11-12(5-8(7)14)16(19)10-3-6(17)1-2-9(10)15(11)18/h1-5,17H

Standard InChI Key:  SPDZOGVSSSQFAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    3.1849    2.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    1.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8956    2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6099    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6106    1.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247    1.0100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3191    2.6593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0338    2.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0374    1.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553    1.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4701    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625    2.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440    2.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1718    2.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147    3.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204    0.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4716    2.6538    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    1.0049    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  4  1  1  0
  9 10  1  0
 10 11  1  0
  2  3  1  0
 11 12  2  0
  5  6  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  6  7  1  0
 13 15  1  0
  7 10  2  0
  8 16  1  0
  1  2  2  0
  7 17  1  0
  9  8  2  0
  1 18  1  0
  8  5  1  0
  2 19  1  0
M  CHG  4   7   1   8   1  16  -1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1288605

   ---

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: 297.10

Molecular Weight (Monoisotopic): 295.9755

AlogP: 2.27

#Rotatable Bonds: ┄

Polar Surface Area: 74.11

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.05

CX Basic pKa: 2.79

CX LogP: 2.09

CX LogD: 0.82

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.39

Np Likeness Score: -0.05

References

1. Lavaggi ML, Nieves M, Cabrera M, Olea-Azar C, López de Ceráin A, Monge A, Cerecetto H, González M..  (2010)  Structural modifications on the phenazine N,N'-dioxide-scaffold looking for new selective hypoxic cytotoxins.,  45  (11): [PMID:20846761] [10.1016/j.ejmech.2010.08.061]

2. Alvarez G, Aguirre-López B, Varela J, Cabrera M, Merlino A, López GV, Lavaggi ML, Porcal W, Di Maio R, González M, Cerecetto H, Cabrera N, Pérez-Montfort R, de Gómez-Puyou MT, Gómez-Puyou A..  (2010)  Massive screening yields novel and selective Trypanosoma cruzi triosephosphate isomerase dimer-interface-irreversible inhibitors with anti-trypanosomal activity.,  45  (12): [PMID:20889239] [10.1016/j.ejmech.2010.09.034]

Source

Source(1):

• Scientific Literature