3-(6-(2,4-Difluorophenyl)-2,4-dioxo-2H-benzo[e][1,3]-oxazin-3(4H)-yl)benzonitrile

ID: ALA3596957

PubChem CID: 71812094

Max Phase: Preclinical

Molecular Formula: C21H10F2N2O3

Molecular Weight: 376.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(-n2c(=O)oc3ccc(-c4ccc(F)cc4F)cc3c2=O)c1

Standard InChI:  InChI=1S/C21H10F2N2O3/c22-14-5-6-16(18(23)10-14)13-4-7-19-17(9-13)20(26)25(21(27)28-19)15-3-1-2-12(8-15)11-24/h1-10H

Standard InChI Key:  QBIJBVAOMNGPFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125    0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2206   -0.4383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5317    3.6272    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    3.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985    3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4907    1.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977    5.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1996    6.4478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6 15  1  0
  7 13  1  0
 11  2  1  0
  3 13  1  0
 11 15  2  0
  9 20  2  0
  2  4  1  0
  9  7  1  0
 14  8  1  0
 12  5  1  0
  1 11  1  0
 18 12  1  0
  8  9  1  0
 12  6  2  0
 17 19  1  0
  7 16  2  0
  2 18  2  0
 13 17  2  0
  1 16  1  0
  3 14  1  0
 19  1  2  0
 14 10  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  8 21  1  0
 27 28  3  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3596957

   3-(6-(2,4-difluorophenyl)-2,4-dioxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)benzonitrile

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: 376.32

Molecular Weight (Monoisotopic): 376.0659

AlogP: 3.76

#Rotatable Bonds: 2

Polar Surface Area: 76.00

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 4.60

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -1.35

References

1. Lee CC, Liu FL, Chen CL, Chen TC, Liu FC, Ahmed Ali AA, Chang DM, Huang HS..  (2015)  Novel inhibitors of RANKL-induced osteoclastogenesis: Design, synthesis, and biological evaluation of 6-(2,4-difluorophenyl)-3-phenyl-2H-benzo[e][1,3]oxazine-2,4(3H)-diones.,  23  (15): [PMID:26081760] [10.1016/j.bmc.2015.06.007]

Source

Source(1):

• Scientific Literature