1-(3-Chloro-4-fluoro-phenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione

ID: ALA4787695

PubChem CID: 148191880

Max Phase: Preclinical

Molecular Formula: C16H6ClF2N3O2

Molecular Weight: 345.69

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2cc(F)ccc2C(=O)c2c1nnn2-c1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C16H6ClF2N3O2/c17-11-6-8(2-4-12(11)19)22-14-13(20-21-22)15(23)10-5-7(18)1-3-9(10)16(14)24/h1-6H

Standard InChI Key:  KGLAAILBKHAJFQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    4.5674  -26.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663  -27.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2743  -27.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725  -26.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812  -26.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9800  -27.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6901  -27.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6924  -26.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4071  -26.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4038  -27.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1858  -27.6463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725  -26.9821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1911  -26.3141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4350  -28.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8840  -29.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329  -29.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9323  -29.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4824  -29.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2306  -28.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6891  -28.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6925  -25.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2817  -29.5404    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1827  -30.7580    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596  -26.1585    0.0000 F   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  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 11 14  1  0
  7 20  2  0
  8 21  2  0
 18 22  1  0
 17 23  1  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4787695

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 345.69

Molecular Weight (Monoisotopic): 345.0117

AlogP: 2.97

#Rotatable Bonds: 1

Polar Surface Area: 64.85

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -1.64

References

1. Pan S,Zhou Y,Wang Q,Wang Y,Tian C,Wang T,Huang L,Nan J,Li L,Yang S.  (2020)  Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO).,  207  [PMID:32871341] [10.1016/j.ejmech.2020.112703]

2. Zhang Y, Hu Z, Zhang J, Ren C, Wang Y..  (2022)  Dual-target inhibitors of indoleamine 2, 3 dioxygenase 1 (Ido1): A promising direction in cancer immunotherapy.,  238  [PMID:35696861] [10.1016/j.ejmech.2022.114524]

Source

Source(1):

• Scientific Literature