methyl 2-(4-(difluoromethyl)phenyl)benzo[d]oxazol-5-yl(ethyl)phosphinate

ID: ALA4776156

PubChem CID: 162643425

Max Phase: Preclinical

Molecular Formula: C17H16F2NO3P

Molecular Weight: 351.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccc(C(F)F)cc3)nc2c1

Standard InChI:  InChI=1S/C17H16F2NO3P/c1-3-24(21,22-2)13-8-9-15-14(10-13)20-17(23-15)12-6-4-11(5-7-12)16(18)19/h4-10,16H,3H2,1-2H3

Standard InChI Key:  HRQWQMCAWNQXIX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.5048  -10.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5037  -11.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2117  -11.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2099   -9.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9185  -10.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9233  -11.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7034  -11.4310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1807  -10.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6956  -10.1065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7956  -11.5951    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0882  -11.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802  -11.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950  -12.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7881  -10.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0766  -10.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9959  -10.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4081  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2245  -11.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6297  -10.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2126  -10.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3975  -10.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4469  -10.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8606  -11.4512    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8504  -10.0359    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  9  1  0
  9  5  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 10 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 16  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776156

   ---

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: 351.29

Molecular Weight (Monoisotopic): 351.0836

AlogP: 5.00

#Rotatable Bonds: 5

Polar Surface Area: 52.33

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.98

References

1. Chatzopoulou M,Emer E,Lecci C,Rowley JA,Casagrande AS,Moir L,Squire SE,Davies SG,Harriman S,Wynne GM,Wilson FX,Davies KE,Russell AJ.  (2020)  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.,  11  (12): [PMID:33335663] [10.1021/acsmedchemlett.0c00405]

2. Chatzopoulou, Maria and 16 more authors.  2020-03-12  Isolation, Structural Identification, Synthesis, and Pharmacological Profiling of 1,2-trans-Dihydro-1,2-diol Metabolites of the Utrophin Modulator Ezutromid.  [PMID:31599580]

3. Babbs, Arran and 19 more authors.  2020-07-23  2-Arylbenzo[d]oxazole Phosphinate Esters as Second-Generation Modulators of Utrophin for the Treatment of Duchenne Muscular Dystrophy.  [PMID:32551645]

4. Chatzopoulou, Maria and 12 more authors.  2020-12-10  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.  [PMID:33335663]

Source

Source(1):

• Scientific Literature