2,8-difluoroindolo[2,1-b]quinazoline-6,12-dione

ID: ALA3087009

PubChem CID: 478643

Max Phase: Preclinical

Molecular Formula: C15H6F2N2O2

Molecular Weight: 284.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2cc(F)ccc2-n2c1nc1ccc(F)cc1c2=O

Standard InChI:  InChI=1S/C15H6F2N2O2/c16-7-1-3-11-9(5-7)15(21)19-12-4-2-8(17)6-10(12)13(20)14(19)18-11/h1-6H

Standard InChI Key:  PNIGSYVPVQBQOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   10.0401   -6.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0390   -7.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7470   -7.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452   -6.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4539   -6.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4527   -7.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1589   -7.7512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1612   -6.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8719   -6.5235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8727   -7.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6513   -7.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6500   -6.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1275   -6.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9359   -6.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2679   -6.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7854   -5.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9786   -5.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1612   -5.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9065   -8.3703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3323   -6.1167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -6.0159    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  2  0
  9  8  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  9  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  8 18  2  0
 11 19  2  0
  1 20  1  0
 15 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3087009

   2,8-Difluoroindolo[2,1-b]quinazoline-6,12-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: 284.22

Molecular Weight (Monoisotopic): 284.0397

AlogP: 2.21

#Rotatable Bonds: ┄

Polar Surface Area: 51.96

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: 2.68

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.50

Np Likeness Score: -0.43

References

1. Yang S, Li X, Hu F, Li Y, Yang Y, Yan J, Kuang C, Yang Q..  (2013)  Discovery of tryptanthrin derivatives as potent inhibitors of indoleamine 2,3-dioxygenase with therapeutic activity in Lewis lung cancer (LLC) tumor-bearing mice.,  56  (21): [PMID:24099220] [10.1021/jm401195n]

2. Li J, Li Y, Yang D, Hu N, Guo Z, Kuang C, Yang Q..  (2016)  Establishment of a human indoleamine 2, 3-dioxygenase 2 (hIDO2) bioassay system and discovery of tryptanthrin derivatives as potent hIDO2 inhibitors.,  123  [PMID:27475108] [10.1016/j.ejmech.2016.07.013]

3. Zhang S, Qi F, Fang X, Yang D, Hu H, Huang Q, Kuang C, Yang Q..  (2018)  Tryptophan 2,3-dioxygenase inhibitory activities of tryptanthrin derivatives.,  160  [PMID:30321802] [10.1016/j.ejmech.2018.10.017]

4.  (2017)  Uses of tryptanthrin and derivative thereof in preparing hldo2 inhibitor, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data