2-(4-((1-(3,4-difluorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)naphtho[1,2-d]oxazole

ID: ALA2430643

PubChem CID: 73346272

Max Phase: Preclinical

Molecular Formula: C26H16F2N4O2

Molecular Weight: 454.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(-n2cc(COc3ccc(-c4nc5c(ccc6ccccc65)o4)cc3)nn2)cc1F

Standard InChI:  InChI=1S/C26H16F2N4O2/c27-22-11-8-19(13-23(22)28)32-14-18(30-31-32)15-33-20-9-5-17(6-10-20)26-29-25-21-4-2-1-3-16(21)7-12-24(25)34-26/h1-14H,15H2

Standard InChI Key:  MBUSAQGZMGUNJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    0.2480  -14.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469  -15.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642  -15.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625  -14.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721  -14.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6729  -15.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824  -15.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000  -15.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851  -14.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0982  -14.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139  -13.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721  -13.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5577  -13.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8231  -12.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6487  -12.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996  -11.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7273  -11.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000  -11.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487  -11.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897  -10.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0171  -10.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4712   -9.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869   -9.6471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4249   -8.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6911   -8.4483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1018   -9.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091   -7.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2829   -7.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2013   -6.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410   -5.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -6.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -5.1737    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8857   -5.8558    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
  6  7  1  0
  7  8  2  0
  8 10  1  0
  9  5  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 12 14  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
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 30 33  1  0
 29 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2430643

   2-[4-[[1-(3,4-Difluorophenyl)triazol-4-yl]methoxy]phenyl]benzo[e][1,3]benzoxazole

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: 454.44

Molecular Weight (Monoisotopic): 454.1241

AlogP: 6.09

#Rotatable Bonds: 5

Polar Surface Area: 65.97

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.03

CX LogP: 5.97

CX LogD: 5.97

Aromatic Rings: 6

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -1.78

References

1. Madabhushi S, Chinthala N, Kanwal A, Kaur G, Banerjee SK.  (2013)  Synthesis and characterization of 2-(4-((1-alkyl or aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)naphtho[1,2-d]oxazoles for protein tyrosine phosphatase 1B inhibitory activity,  [10.1007/s00044-013-0784-0]

Source

Source(1):

• Scientific Literature