2-Bromo-3-(((1-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)-1H-1,2,3-triazol-4-yl)methyl)amino)naphthalene-1,4-dione

ID: ALA3114584

PubChem CID: 76310540

Max Phase: Preclinical

Molecular Formula: C23H13BrN4O4

Molecular Weight: 489.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(n2cc(CNC3=C(Br)C(=O)c4ccccc4C3=O)nn2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C23H13BrN4O4/c24-19-20(23(32)16-8-4-3-7-15(16)22(19)31)25-10-12-11-28(27-26-12)17-9-18(29)13-5-1-2-6-14(13)21(17)30/h1-9,11,25H,10H2

Standard InChI Key:  YLJOKDHOHHJDFB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    0.4027  -14.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016  -15.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1163  -15.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145  -14.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299  -14.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332  -15.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524  -15.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2727  -15.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693  -14.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455  -14.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410  -13.3485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546  -16.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824  -14.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981  -14.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112  -14.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1608  -14.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7109  -13.8909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962  -13.1777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4899  -13.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5282  -13.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8647  -14.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6816  -14.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0088  -13.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8317  -13.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1671  -14.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9856  -14.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4695  -13.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1292  -12.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116  -12.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6716  -12.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0172  -15.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860  -15.8305    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  2  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 20 21  2  0
 20 23  1  0
 21 22  1  0
 22 25  1  0
 24 23  1  0
 17 20  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 23 30  2  0
 22 31  2  0
  8 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114584

   2-Bromo-3-[[1-(1,4-dioxonaphthalen-2-yl)triazol-4-yl]methylamino]naphthalene-1,4-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: 489.29

Molecular Weight (Monoisotopic): 488.0120

AlogP: 2.97

#Rotatable Bonds: 4

Polar Surface Area: 111.02

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.14

CX LogD: 2.14

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -0.30

References

1. da Cruz EH, Hussene CM, Dias GG, Diogo EB, de Melo IM, Rodrigues BL, da Silva MG, Valença WO, Camara CA, de Oliveira RN, de Paiva YG, Goulart MO, Cavalcanti BC, Pessoa C, da Silva Júnior EN..  (2014)  1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.,  22  (5): [PMID:24530030] [10.1016/j.bmc.2014.01.033]

Source

Source(1):

• Scientific Literature